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Home > Catalytic asymmetric dearomatization (CADA) reaction-enabled total synthesis of indole-based natural products

Catalytic asymmetric dearomatization (CADA) reaction-enabled total synthesis of indole-based natural products


Chao Zheng and Shu-Li You

 

 

1. Introduction
The positive interplay between the studies on natural product synthesis and synthetic methodology development constitutes the major theme of fundamental organic chemistry. The fascinating structures of various natural products serve as the inspiration and driving force of endless emerging and evolving unprecedented synthetic methods. On the other hand, natural product synthesis is generally regarded as a premier stage, where a synthetic method can exhibit its practicality and robustness.

 

Indole-based polycyclic structures have constantly received intensive research interests due to their wide occurrence in numerous alkaloids that possess diverse biological activities Dearomatization of indole derivatives has long been viewed as an attractive strategy to readily access sophisticated spiro or fused polycyclic indoline scaffolds. Accordingly, Qin et al. developed an elegant cascade (or stepwise) reaction of cyclopropanation/ring-opening/iminium (CRI) cyclization of tryptamine derivatives, which enables the efficient assembly of a variety of indoline alkaloids.8 Meanwhile, Ma and co-workers
carried out systematic studies on intramolecular dearomative oxidative coupling (IDOC) reactions of indoles and accomplished the total synthesis of many indoline alkaloids.

 

In recent years, catalytic asymmetric dearomatization (CADA) reactions have been recognized as powerful methods for the conversion of readily available planar aromatic feedstocks to three-dimensional polycyclic molecules.10–18 Particularly, the synthesis of many indole-based natural products becomes viable with the key ring system and the stereochemistry being established via a CADA reaction. A major advantage of these syntheses is that they do not rely on the chiral pool strategy. The absolute conguration of the product is solely controlled by the chiral catalyst. Therefore, not only natural products themselves, but also their corresponding unnatural enantiomers, diastereoisomers, and even libraries of analogs can be easily synthesized, which is of great importance in medicinal chemistry.

 

Herein, we summarize the most recent progress on the total synthesis of indole-based natural products enabled by an asymmetric dearomatization reaction as the key step (Fig. 1). Several ring-forming strategies for the construction of key polycyclic scaffolds will be rst highlighted. Then, the various applications of asymmetric dearomatization reactions in the total syntheses of these natural products will be discussed accordingly. Finally, we present a personal perspective of this dynamic researcheld.

 

2. General strategies for the formation of key ring systems
In general, a series of ring-formation strategies have been developed in the total synthesis of indole-based natural products via a CADA reaction (Fig. 2). Most of these strategies take advantage of
the inherent strong nucleophilicity of the C3 position of 3-substituted indoles and the electrophilicity of 3,3-disubstituted indolenine cations (types I to IV). By devising appropriately tethered nucleophiles and electrophiles, cascade cyclization reactions may be triggered. On the other hand, the recent enantioselective total synthesis of (+)-hinckdentine A involved a dearomative Hecktype cyclization, which can be regarded as the connection between the C2 position of indole with an electrophile (type V). Notably, the asymmetric dearomatization of indole derivatives via a visiblelight-mediated sequential single-electron transfer process has also emerged, which allowed the formal installation of an external nucleophile at the C3 position of indole with concomitant cyclization (type VI). By employing these strategies, spiro, fused, and even bridged polycyclic scaffolds can be assembled by carefully manipulating the reaction sequence. In the following sections, detailed discussions will be presented on how these strategies have been applied in the construction of the core structures of indole-based natural products.


3. Type I cyclization
The most frequently employed strategy takes advantage of indole substrates possessing a pendant nucleophile on the C3 position, where tryptamine/tryptophol derivatives are among the commonly used substrates. A Friedel–Cras-type addition with an external electrophile generates a 3,3-disubstituted indolenine intermediate whose iminium moiety is readily trapped by the nucleophilic side chain, yielding the corresponding hexahydropyrrolo[2,3-b]indole (HPI) or tetrahydro-2H-furo[2,3-b]indole core structures, which lays a solid foundation for further synthetic elaborations.


In the past several years, signicant contributions have been made in the area of catalytic asymmetric dearomatization reactions, which have brought to the synthetic community a series of novel disconnection strategies in the total synthesis of diverse natural products. As the most prominent examples, many elegant asymmetric total syntheses of indole-based polycyclic alkaloids have been reported. As presented in the previous sections, these syntheses take advantages of both rational design of the substrates and the newly disclosed reactivity under the theme of catalytic asymmetric dearomatization.

 

Undoubtedly, these achievements will stimulate further investigations in related areas. We believe that future studies may be focused on the application of more strategies in catalytic asymmetric dearomatization. Most of the syntheses discussed herein largely rely on the manipulations of the nucleophilicity/electrophilicity of the substituted indole substrates at the ipso position. However, the rapid development of visible-lightmediated reactions via the single-electron transfer process provide new possibilities for exploring asymmetric dearomatization reactions, which have been exemplied by the recent studies from Knowles' group.93 In addition, Sarlah and coworkers performed systematic studies on visible-lightmediated dearomatization of substituted benzenes with an arenophile, which pave the way for the efficient synthesis of diverse natural products.

 

Overall, considering that continuing developments are being made in the area of catalytic asymmetric dearomatization reactions, we feel quite condent that this powerful strategy will end broad applications in the journey of natural product total synthesis.

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MF:C6H8N4O3 MW:184.1527

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3H-Purin-6-amine, 3-(diphenylmethyl)-

Catalog No.:AG0005P7 MDL No.:

MF:C18H15N5 MW:301.3452

CAS No. 10184-20-0

9H-Purin-6-amine, N-(diphenylmethyl)-, hydrochloride (1:1)

Catalog No.:AG0005P6 MDL No.:

MF:C18H16ClN5 MW:337.8061

CAS No. 10184-51-7

9H-Purin-6-amine, 9-methyl-, 1-oxide

Catalog No.:AG0005P5 MDL No.:

MF:C6H7N5O MW:165.1527

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Phosphonic acid, P-(1-hydroxyethyl)-, dimethyl ester

Catalog No.:AG0005P4 MDL No.:

MF:C4H11O4P MW:154.1015

CAS No. 10184-68-6

Phosphonic acid, (1-hydroxy-1-methylethyl)-, dimethyl ester (6CI,7CI,8CI,9CI)

Catalog No.:AG0005P3 MDL No.:

MF:C5H13O4P MW:168.1281

CAS No. 10184-96-0

Propanedioic acid, 2-(1H-indol-3-ylmethylene)-, 1,3-diethyl ester

Catalog No.:AG0005P2 MDL No.:MFCD00022744

MF:C16H17NO4 MW:287.3105

CAS No. 10184-98-2

Propanedioic acid, 2-(1H-indol-3-ylmethyl)-, 1,3-diethyl ester

Catalog No.:AG0005P1 MDL No.:

MF:C16H19NO4 MW:289.3264

CAS No. 101842-77-7

9,12-Octadecadienoic acid (9Z,12Z)-, 1-hexyl-12-(isohexadecyloxy)-12-oxododecyl ester (9CI)

Catalog No.:AG0005OU MDL No.:

MF:C52H98O4 MW:787.3321

CAS No. 101843-14-5

Anthracenone

Catalog No.:AG0005OT MDL No.:

MF:C14H10O MW:194.2286

CAS No. 101843-38-3

Dodecanoic acid, 1-(sulfophenyl) ester

Catalog No.:AG0005OS MDL No.:

MF:C18H28O5S MW:356.4769

CAS No. 101843-39-4

Benzene, tetramethoxy(2-propen-1-yl)-

Catalog No.:AG0005OR MDL No.:MFCD10037571

MF:C13H18O4 MW:238.2796

CAS No. 101843-94-1

1H-1,2,4-Triazole-3-carboxamide, 1-(2,3,5-tri-O-butyl-β-D-ribofuranosyl)-

Catalog No.:AG0005OQ MDL No.:

MF:C20H36N4O5 MW:412.5236

CAS No. 1018437-11-0

1-Piperidineacetonitrile, 4-hydroxy-α-phenyl-

Catalog No.:AG0005OL MDL No.:MFCD10014842

MF:C13H16N2O MW:216.2789

CAS No. 101844-21-7

2-Propen-1-ol, 3-(dimethylphenylsilyl)-, (2E)-

Catalog No.:AG0005OP MDL No.:

MF:C11H16OSi MW:192.3296

CAS No. 101844-22-8

2-Propen-1-ol, 2-(dimethylphenylsilyl)-

Catalog No.:AG0005PT MDL No.:

MF:C11H16OSi MW:192.3296

CAS No. 1018441-16-1

1H-Pyrrolo[2,3-b]pyridin-6-amine, N-methyl-

Catalog No.:AG0005PK MDL No.:MFCD09910035

MF:C8H9N3 MW:147.1772

CAS No. 1018443-00-9

Pyrrolidine, 3-(1-azetidinyl)-, hydrochloride (1:1)

Catalog No.:AG0005PJ MDL No.:

MF:C7H15ClN2 MW:162.6604

CAS No. 1018443-01-0

Carbamic acid, N-(3-methyl-3-azetidinyl)-, 1,1-dimethylethyl ester

Catalog No.:AG0005PI MDL No.:MFCD11974378

MF:C9H18N2O2 MW:186.2514

CAS No. 1018443-32-7

Pyrrolo[3,4-b]pyrrole-1(2H)-carboxylic acid, hexahydro-, 1,1-dimethylethyl ester, (3aR,6aR)-rel-

Catalog No.:AG0005PH MDL No.:MFCD18917061

MF:C11H20N2O2 MW:212.2887

CAS No. 1018446-60-0

1H-Pyrazole-3-carboxylic acid, 5-hydroxy-, methyl ester

Catalog No.:AG0005PG MDL No.:MFCD09878841

MF:C5H6N2O3 MW:142.1127

CAS No. 1018446-95-1

1H-Pyrazole-1-carboxylic acid, 4-amino-, 1,1-dimethylethyl ester

Catalog No.:AG0005PF MDL No.:MFCD20697038

MF:C8H13N3O2 MW:183.2077

CAS No. 1018450-37-7

Benzenamine, 4-chloro-3-fluoro-2-iodo-

Catalog No.:AG0005PE MDL No.:MFCD18250658

MF:C6H4ClFIN MW:271.4585

CAS No. 1018453-54-7

2-Piperidinone, 6-ethyl-, (6R)-

Catalog No.:AG0005PD MDL No.:

MF:C7H13NO MW:127.1842

CAS No. 101846-83-7

1-Naphthalenemethanamine, N-[[4-(1,1-dimethylethyl)phenyl]methyl]-

Catalog No.:AG0005PS MDL No.:

MF:C22H25N MW:303.4406

CAS No. 1018473-22-7

1H-Pyrazol-5-amine, 1-(6-chloro-4-pyrimidinyl)-3-methyl-

Catalog No.:AG0005PC MDL No.:MFCD19440630

MF:C8H8ClN5 MW:209.6356

CAS No. 1018473-31-8

1,3-Benzenediamine, 4-methyl-N3-[3-methyl-1-[6-(methylamino)-4-pyrimidinyl]-1H-pyrazol-5-yl]-

Catalog No.:AG0005PB MDL No.:

MF:C16H19N7 MW:309.3690

CAS No. 1018478-41-5

1-Piperidinecarboxylic acid, 3-hydroxy-4-[4-[[(2S)-3-methoxy-2-methylpropoxy]methyl]phenyl]-5-[(triphenylmethoxy)methyl]-, phenylmethyl ester, (3R,4R,5S)-

Catalog No.:AG0005PA MDL No.:

MF:C45H49NO6 MW:699.8737

CAS No. 101848-19-5

Carbamic acid, [5-(methylthio)-1,2,4-thiadiazol-3-yl]-, methyl ester (9CI)

Catalog No.:AG0005PR MDL No.:MFCD00846949

MF:C5H7N3O2S2 MW:205.2580

CAS No. 101848-25-3

L-Threonine, L-isoleucyl-L-threonyl-

Catalog No.:AG0005PQ MDL No.:

MF:C14H27N3O6 MW:333.3807

CAS No. 101848-26-4

Glycine, N-[N-[N-[N-[N-[N-(N-L-leucyl-L-phenylalanyl)-L-valyl]-L-valyl]-L-threonyl]-L-leucyl]-L-valyl]- (9CI)

Catalog No.:AG0005PP MDL No.:

MF:C42H70N8O10 MW:847.0528

CAS No. 101848-68-4

1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-, mixt. with 1-(2,4-dichlorophenyl)-2-(3-pyridinyl)ethanone O-methyloxime (9CI)

Catalog No.:AG0005PO MDL No.:

MF: MW:

CAS No. 101849-21-2

1,1,3,3-Propanetetrol, 2-heptyl-

Catalog No.:AG0005PN MDL No.:

MF:C10H22O4 MW:206.2793

CAS No. 101849-67-6

Stannane, [(1Z)-1-(2-chloroethyl)-1-propen-1-yl]trimethyl-

Catalog No.:AG0005PM MDL No.:

MF:C8H17ClSn MW:267.3746

CAS No. 101849-78-9

2H-Cyclopenta[b]furan-2-one, hexahydro-4-[(1E,3S,5S)-5-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-nonen-1-yl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]-, (3aR,4R,5R,6aS)-

Catalog No.:AG0005PL MDL No.:MFCD23115482

MF:C27H44O6 MW:464.6347

CAS No. 10185-00-9

2H-1-Benzopyran-3-carboxamide

Catalog No.:AG0005PY MDL No.:

MF:C10H9NO2 MW:175.1840

CAS No. 10185-29-2

2,5-Pyrrolidinedione, 3-(1H-indol-3-yl)-

Catalog No.:AG0005PX MDL No.:MFCD03192751

MF:C12H10N2O2 MW:214.2200

CAS No. 10185-45-2

9H-Carbazole-9-ethanol, 3-nitro-

Catalog No.:AG0005PW MDL No.:

MF:C14H12N2O3 MW:256.2567

CAS No. 10185-46-3

2H-1-Benzopyran-3-methanamine, 3,4-dihydro-

Catalog No.:AG0005PV MDL No.:MFCD04114627

MF:C10H13NO MW:163.2163

CAS No. 10185-62-3

Benzenesulfonyl chloride, 3-(5-methyl-1,2,4-oxadiazol-3-yl)-

Catalog No.:AG0005PU MDL No.:MFCD06797486

MF:C9H7ClN2O3S MW:258.6815

CAS No. 10185-65-6

1,2,4-Oxadiazole, 5-ethyl-3-(4-nitrophenyl)-

Catalog No.:AG0005QN MDL No.:MFCD09972166

MF:C10H9N3O3 MW:219.1968

CAS No. 10185-66-7

1,2,4-Oxadiazole, 5-butyl-3-(3-nitrophenyl)-

Catalog No.:AG0005QM MDL No.:MFCD10699664

MF:C12H13N3O3 MW:247.2499

CAS No. 10185-68-9

Benzenamine, 4-(5-methyl-1,2,4-oxadiazol-3-yl)-

Catalog No.:AG0005QL MDL No.:MFCD08435856

MF:C9H9N3O MW:175.1873

CAS No. 10185-69-0

Benzenamine, 3-(5-methyl-1,2,4-oxadiazol-3-yl)-

Catalog No.:AG0005QK MDL No.:MFCD08443707

MF:C9H9N3O MW:175.1873

CAS No. 10185-71-4

Benzenamine, 4-(5-ethyl-1,2,4-oxadiazol-3-yl)-

Catalog No.:AG0005QJ MDL No.:

MF:C10H11N3O MW:189.2138

CAS No. 101850-43-5

Pyrimido[5,4-d]pyrimidin-4-amine, 2,8-dichloro-N,N-diethyl-

Catalog No.:AG0005QI MDL No.:

MF:C10H11Cl2N5 MW:272.1338

CAS No. 101850-71-9

1H-Pyrazol-5-amine, 4-(1H-1,2,4-triazol-1-yl)-1-(2,4,6-trichlorophenyl)-

Catalog No.:AG0005QH MDL No.:

MF:C11H7Cl3N6 MW:329.5725

CAS No. 1018502-06-1

Benzamide, 3-amino-4-chloro-N-(3-pyridinylmethyl)-

Catalog No.:AG0005Q4 MDL No.:MFCD10021697

MF:C13H12ClN3O MW:261.7069

CAS No. 1018505-59-3

2-Pyridinamine, 5-(4-ethyl-1-piperazinyl)-

Catalog No.:AG0005Q3 MDL No.:MFCD10009575

MF:C11H18N4 MW:206.2874

CAS No. 1018506-33-6

Benzenepropanamide, 2-amino-N,N-dimethyl-

Catalog No.:AG0005Q2 MDL No.:MFCD10022148

MF:C11H16N2O MW:192.2575

CAS No. 101851-40-5

Hydrazine, (4-chloro-1-naphthalenyl)-

Catalog No.:AG0005QG MDL No.:MFCD06738784

MF:C10H9ClN2 MW:192.6449

CAS No. 101853-07-0

Methanone, bis[4-(dibutylamino)phenyl]-

Catalog No.:AG0005QF MDL No.:

MF:C29H44N2O MW:436.6725

CAS No. 101853-22-9

Silacyclohepta-2,4,6-triene

Catalog No.:AG0005QE MDL No.:

MF:C6H8Si MW:108.2132

CAS No. 101853-43-4

Benzoic acid, 2-hydroxy-, cyclohexylmethyl ester

Catalog No.:AG0005QD MDL No.:

MF:C14H18O3 MW:234.2909

CAS No. 101853-47-8

Decanoic acid,5-hydroxy-, methyl ester

Catalog No.:AG0005QC MDL No.:

MF:C11H22O3 MW:202.2906

CAS No. 101853-49-0

Octanoic acid, 5-hydroxy-, methyl ester

Catalog No.:AG0005QB MDL No.:

MF:C9H18O3 MW:174.2374

CAS No. 101853-53-6

2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(3,3-dimethyloctyl)-5-ethyl-

Catalog No.:AG0005QA MDL No.:

MF:C16H28N2O3 MW:296.4051

CAS No. 101853-75-2

1H-Imidazole, 2,4,5-tribromo-1-[(3,4-dimethoxyphenyl)methyl]-

Catalog No.:AG0005Q9 MDL No.:

MF:C12H11Br3N2O2 MW:454.9399

CAS No. 101853-76-3

1H-Imidazole, 4,5-dibromo-1-(methoxymethyl)-

Catalog No.:AG0005Q8 MDL No.:

MF:C5H6Br2N2O MW:269.9219

CAS No. 101853-81-0

1H-Imidazole, 4,5-dibromo-2-(ethylthio)-1-(methoxymethyl)-

Catalog No.:AG0005Q7 MDL No.:

MF:C7H10Br2N2OS MW:330.0401

CAS No. 101853-86-5

1H-Imidazole, 4,5-dibromo-1-(phenylmethyl)-2-(phenylthio)-

Catalog No.:AG0005Q6 MDL No.:

MF:C16H12Br2N2S MW:424.1529

CAS No. 101853-88-7

1H-Imidazole-5-carboxaldehyde, 4-bromo-1-[(4-methoxyphenyl)methyl]-

Catalog No.:AG0005Q5 MDL No.:

MF:C12H11BrN2O2 MW:295.1319

CAS No. 1018533-19-1

Piperidine, 4-[[(1-methylethyl)sulfonyl]methyl]-

Catalog No.:AG0005Q1 MDL No.:MFCD23703555

MF:C9H19NO2S MW:205.3177

CAS No. 1018537-04-6

Benzenesulfonamide, 4-(2-chloroethyl)-N-propyl-

Catalog No.:AG0005Q0 MDL No.:

MF:C11H16ClNO2S MW:261.7682

CAS No. 1018537-08-0

Benzenesulfonamide, N-butyl-4-(2-chloroethyl)-

Catalog No.:AG0005PZ MDL No.:

MF:C12H18ClNO2S MW:275.7948

CAS No. 1018537-12-6

Benzenesulfonamide, 4-(2-chloroethyl)-N-cyclopentyl-

Catalog No.:AG0005QY MDL No.:MFCD10020933

MF:C13H18ClNO2S MW:287.8055

CAS No. 1018537-40-0

Benzenesulfonamide, 4-(2-chloroethyl)-N,N-diethyl-

Catalog No.:AG0005QX MDL No.:

MF:C12H18ClNO2S MW:275.7948

CAS No. 1018537-56-8

1H-Indole, 1-[[4-(2-chloroethyl)phenyl]sulfonyl]-2,3-dihydro-

Catalog No.:AG0005QW MDL No.:

MF:C16H16ClNO2S MW:321.8217

CAS No. 1018537-64-8

Benzenesulfonamide, 4-(2-chloroethyl)-N-(2-ethylphenyl)-

Catalog No.:AG0005QV MDL No.:

MF:C16H18ClNO2S MW:323.8376

CAS No. 101854-08-4

1,3-Dioxolane, 2-methyl-2,4-diphenyl-

Catalog No.:AG0005RC MDL No.:

MF:C16H16O2 MW:240.2970

CAS No. 101854-25-5

L-Proline, 1-[N-[N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl]-L-valyl]- (9CI)

Catalog No.:AG0005RB MDL No.:

MF:C24H35N3O6 MW:461.5512

CAS No. 101854-42-6

Butanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(phenylmethoxy)carbonyl]amino]-, (R)-, compd. with N-cyclohexylcyclohexanamine (1:1) (9CI)

Catalog No.:AG0005RA MDL No.:MFCD00798628

MF:C29H47N3O6 MW:533.7000

CAS No. 101854-80-2

Pyrimidine, 1,4-dihydro-2-methyl-

Catalog No.:AG0005R9 MDL No.:

MF:C5H8N2 MW:96.1304

CAS No. 1018544-60-9

1-Piperazinecarboxylic acid, 4-[2-amino-1-(4-bromophenyl)ethyl]-, 1,1-dimethylethyl ester

Catalog No.:AG0005QU MDL No.:

MF:C17H26BrN3O2 MW:384.3112

CAS No. 1018548-98-5

β-Alanine, N-[[(2-phenylethyl)amino]carbonyl]-

Catalog No.:AG0005QT MDL No.:

MF:C12H16N2O3 MW:236.2670

CAS No. 1018549-00-2

2H-Indol-2-one, 1,3-dihydro-3-(hydroxymethylene)-5-methoxy-

Catalog No.:AG0005QS MDL No.:

MF:C10H9NO3 MW:191.1834

CAS No. 101855-18-9

4H-Naphth[1,2-d][1,3]oxazin-4-one, 2-methyl-

Catalog No.:AG0005R8 MDL No.:

MF:C13H9NO2 MW:211.2161

CAS No. 101855-37-2

2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-, 1-methylethyl ester

Catalog No.:AG0005R7 MDL No.:

MF:C13H13NO4 MW:247.2466

CAS No. 101855-91-8

Methanone, bis[2-chloro-5-(trifluoromethyl)phenyl]-

Catalog No.:AG0005R6 MDL No.:

MF:C15H6Cl2F6O MW:387.1040

CAS No. 1018555-33-3

1-Propanone, 1-[4-(aminomethyl)-1-piperidinyl]-2,2-dimethyl-

Catalog No.:AG0005QR MDL No.:

MF:C11H22N2O MW:198.3052

CAS No. 1018557-32-8

Piperidine, 4-[(propylsulfonyl)methyl]-

Catalog No.:AG0005QQ MDL No.:MFCD10017396

MF:C9H19NO2S MW:205.3177

CAS No. 1018564-07-2

Benzamide, 4-amino-3-methyl-N-(3-pyridinylmethyl)-

Catalog No.:AG0005QP MDL No.:MFCD10022000

MF:C14H15N3O MW:241.2884

CAS No. 1018565-99-5

1(2H)-Quinolineacetic acid, 3,4-dihydro-α-oxo-

Catalog No.:AG0005QO MDL No.:MFCD10018451

MF:C11H11NO3 MW:205.2099

CAS No. 101857-31-2

1,2,5-Selenadiazole-3-carbonyl chloride

Catalog No.:AG0005R5 MDL No.:

MF:C3HClN2OSe MW:195.4658

CAS No. 101857-33-4

1,2-Propanediamine, 3-[(tetrahydro-2H-pyran-2-yl)oxy]-

Catalog No.:AG0005R4 MDL No.:

MF:C8H18N2O2 MW:174.2407

CAS No. 101857-37-8

1,2-Propanediamine, 3-methoxy-

Catalog No.:AG0005R3 MDL No.:MFCD19204176

MF:C4H12N2O MW:104.1509

CAS No. 101857-61-8

1,2-Oxathiin, 3-bromo-4-(bromomethyl)-6-methyl-, 2,2-dioxide

Catalog No.:AG0005R2 MDL No.:

MF:C6H6Br2O3S MW:317.9830

CAS No. 101858-16-6

Hydrazinecarboxamide, N-[3-(diethylamino)propyl]-2-[(5-nitro-2-furanyl)methylene]-

Catalog No.:AG0005R1 MDL No.:

MF:C13H21N5O4 MW:311.3369

CAS No. 101858-22-4

8-Azabicyclo[3.2.1]octane-8-butanol, 3-hydroxy-α,α,3-triphenyl-

Catalog No.:AG0005R0 MDL No.:

MF:C29H33NO2 MW:427.5778

CAS No. 101858-24-6

8-Azabicyclo[3.2.1]octan-3-ol, 3-phenyl-8-(2-phenylethyl)-

Catalog No.:AG0005QZ MDL No.:

MF:C21H25NO MW:307.4293

CAS No. 101858-27-9

9-Octadecenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-

Catalog No.:AG0005RU MDL No.:

MF:C26H43NO3 MW:417.6245

CAS No. 101858-33-7

Octanimidic acid, N-methoxy-, methyl ester

Catalog No.:AG0005RT MDL No.:MFCD01711119

MF:C10H21NO2 MW:187.2792

CAS No. 101859-28-3

2-Butenoic acid, 4-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexyl]-, methyl ester, [1α(Z),2β]- (9CI)

Catalog No.:AG0005RS MDL No.:

MF:C17H32O3Si MW:312.5197

CAS No. 101859-37-4

2-Pentenoic acid, 5-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexyl]-, methyl ester, [1α(Z),2β]- (9CI)

Catalog No.:AG0005RR MDL No.:

MF:C18H34O3Si MW:326.5463

CAS No. 101859-47-6

2-Pentenoic acid, 5-[2-[(4-bromophenyl)methoxy]cyclohexyl]-, methyl ester, [1α(Z),2β]- (9CI)

Catalog No.:AG0005RQ MDL No.:

MF:C19H25BrO3 MW:381.3040

CAS No. 101859-54-5

2-Pentenoic acid, 5-[2-[bis(4-chlorophenyl)methoxy]cyclohexyl]-, methyl ester, [1α(Z),2β]- (9CI)

Catalog No.:AG0005RP MDL No.:

MF:C25H28Cl2O3 MW:447.3940

CAS No. 101859-91-0

Hydrazine, 5-hexen-1-yl-

Catalog No.:AG0005RO MDL No.:

MF:C6H14N2 MW:114.1888

CAS No. 10186-22-8

2H-Pyran-2-one, tetrahydro-6-(2-phenylethyl)-

Catalog No.:AG0005S1 MDL No.:

MF:C13H16O2 MW:204.2649

CAS No. 10186-26-2

Butanedioic acid, 2,2-diphenyl-

Catalog No.:AG0005S0 MDL No.:

MF:C16H14O4 MW:270.2800

CAS No. 10186-63-7

Propanoic acid, 2,3,3,3-tetrafluoro-2-methoxy-, methyl ester

Catalog No.:AG0005RZ MDL No.:MFCD00155951

MF:C5H6F4O3 MW:190.0930

CAS No. 10186-64-8

Propanoic acid, 2,3,3,3-tetrafluoro-2-methoxy-

Catalog No.:AG0005RY MDL No.:MFCD20638862

MF:C4H4F4O3 MW:176.0664

CAS No. 10186-65-9

Propanamide, 2,3,3,3-tetrafluoro-2-methoxy-

Catalog No.:AG0005RX MDL No.:MFCD00193112

MF:C4H5F4NO2 MW:175.0816

CAS No. 10186-66-0

Propanoic acid, 2-ethoxy-2,3,3,3-tetrafluoro-, ethyl ester

Catalog No.:AG0005RW MDL No.:MFCD00205158

MF:C7H10F4O3 MW:218.1461

CAS No. 10186-73-9

Propanoic acid, 2-bromo-2,3,3,3-tetrafluoro-, ethyl ester

Catalog No.:AG0005RV MDL No.:MFCD00153721

MF:C5H5BrF4O2 MW:252.9896

CAS No. 101860-03-1

12,14-Nonacosadiynoic acid

Catalog No.:AG0005RN MDL No.:

MF:C29H50O2 MW:430.7061

CAS No. 101860-05-3

Arsine, bis[(trimethylsilyl)methyl]-

Catalog No.:AG0005RM MDL No.:

MF:C8H23AsSi2 MW:250.3608

CAS No. 101860-51-9

2-Thiazolidinone, 4-acetyl-3-[(4-methoxyphenyl)methyl]-, (4R)-

Catalog No.:AG0005RL MDL No.:

MF:C13H15NO3S MW:265.3281

CAS No. 101860-71-3

Quinoline, 3-chloro-6-nitro-

Catalog No.:AG0005RK MDL No.:

MF:C9H5ClN2O2 MW:208.6012

CAS No. 101860-74-6

4H-1-Benzopyran-4-one, 7-chloro-

Catalog No.:AG0005RJ MDL No.:

MF:C9H5ClO2 MW:180.5878

CAS No. 101860-97-3

3-Pyridineacetic acid, 2-amino-

Catalog No.:AG0005RI MDL No.:MFCD11848318

MF:C7H8N2O2 MW:152.1506

CAS No. 1018600-42-4

Benzamide, 4-(3-aminopropoxy)-

Catalog No.:AG0005RD MDL No.:MFCD10037139

MF:C10H14N2O2 MW:194.2304

CAS No. 101861-00-1

5-Pyrimidinecarboxaldehyde, 1,6-dihydro-2,4-dimethyl-6-oxo-

Catalog No.:AG0005RH MDL No.:

MF:C7H8N2O2 MW:152.1506

CAS No. 101861-10-3

4H-Pyrazolo[3,4-d]pyrimidin-4-one, 6-ethyl-1,5-dihydro-

Catalog No.:AG0005RG MDL No.:

MF:C7H8N4O MW:164.1646

CAS No. 101861-35-2

[1,2,4]Triazolo[1,5-a]pyrimidin-7-ol, 5-ethyl-

Catalog No.:AG0005RF MDL No.:

MF:C7H8N4O MW:164.1646

CAS No. 101861-36-3

6(5H)-Pteridinone, 7,8-dihydro-7-hydroxy-5-methyl-

Catalog No.:AG0005RE MDL No.:

MF:C7H8N4O2 MW:180.1640

CAS No. 101861-40-9

2-Thiophenecarboxylic acid, 5-(ethylthio)-

Catalog No.:AG0005SQ MDL No.:MFCD00738671

MF:C7H8O2S2 MW:188.2672

CAS No. 101861-47-6

Quinoxaline, 2-methoxy-6-nitro-

Catalog No.:AG0005SP MDL No.:

MF:C9H7N3O3 MW:205.1702

CAS No. 101861-53-4

Benzoic acid, 2-(acetylamino)-4-bromo-

Catalog No.:AG0005SO MDL No.:MFCD12805958

MF:C9H8BrNO3 MW:258.0687

CAS No. 101861-59-0

Quinoline, 3,5-dibromo-

Catalog No.:AG0005SN MDL No.:

MF:C9H5Br2N MW:286.9507

CAS No. 101861-61-4

4-Quinolinol, 6-chloro-3-nitro-

Catalog No.:AG0005SM MDL No.:MFCD09800425

MF:C9H5ClN2O3 MW:224.6006

CAS No. 101861-63-6

1H-Indole-2-carboxylic acid, 4,6-dichloro-

Catalog No.:AG0005SL MDL No.:MFCD00209870

MF:C9H5Cl2NO2 MW:230.0475

CAS No. 1018610-80-4

Piperazine, 2-(4-methoxyphenyl)-1-methyl-

Catalog No.:AG0005SJ MDL No.:

MF:C12H18N2O MW:206.2841

CAS No. 1018612-26-4

2-Propenoic acid, 3-(4-bromo-1H-indol-3-yl)-

Catalog No.:AG0005SI MDL No.:

MF:C11H8BrNO2 MW:266.0907

CAS No. 1018614-94-2

Benzeneacetic acid, α,α-dimethyl-4-(4-morpholinyl)-

Catalog No.:AG0005SH MDL No.:

MF:C14H19NO3 MW:249.3056

CAS No. 1018616-74-4

Quinoline, 2-chloro-8-methyl-3-phenyl-

Catalog No.:AG0005SG MDL No.:

MF:C16H12ClN MW:253.7262

CAS No. 101862-42-4

5-Isoxazolemethanol, 3-(3-chlorophenyl)-

Catalog No.:AG0005SK MDL No.:MFCD19105424

MF:C10H8ClNO2 MW:209.6290

CAS No. 1018637-87-0

1H-Indole-2-ethanamine, 6-bromo-

Catalog No.:AG0005SF MDL No.:MFCD10035470

MF:C10H11BrN2 MW:239.1117

CAS No. 1018656-53-5

Morpholine, 2-(2-pyridinyl)-

Catalog No.:AG0005SE MDL No.:MFCD10035254

MF:C9H12N2O MW:164.2044

CAS No. 1018656-57-9

Morpholine, 2-(4-pyridinyl)-

Catalog No.:AG0005SD MDL No.:MFCD10035256

MF:C9H12N2O MW:164.2044

CAS No. 1018660-79-1

Benzeneacetic acid, α,α-dimethyl-4-(1-pyrrolidinyl)-

Catalog No.:AG0005SC MDL No.:

MF:C14H19NO2 MW:233.3062

CAS No. 1018660-87-1

Benzeneacetic acid, α,α-dimethyl-4-(4-methyl-1-piperazinyl)-

Catalog No.:AG0005SB MDL No.:

MF:C15H22N2O2 MW:262.3474

CAS No. 1018662-21-9

3-Isoxazolemethanamine, 5-(4-methoxyphenyl)-

Catalog No.:AG0005SA MDL No.:MFCD09864171

MF:C11H12N2O2 MW:204.2252

CAS No. 1018663-45-0

3-Cyclopentapyrazolecarboxaldehyde, 1,4,5,6-tetrahydro-

Catalog No.:AG0005S9 MDL No.:MFCD10036254

MF:C7H8N2O MW:136.1512

CAS No. 1018665-73-0

Benzenepropanol, β-amino-2-methoxy-

Catalog No.:AG0005S8 MDL No.:

MF:C10H15NO2 MW:181.2316

CAS No. 1018667-18-9

1,2-Pyrrolidinedicarboxylic acid, 4-amino-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-rel-

Catalog No.:AG0005S7 MDL No.:

MF:C11H20N2O4 MW:244.2875

CAS No. 1018678-37-9

Methyl 4-amino-2-chloronicotinate

Catalog No.:AG0005S6 MDL No.:MFCD20726014

MF:C7H7ClN2O2 MW:186.5957

CAS No. 1018678-38-0

3-Pyridinecarboxylic acid, 4-amino-2-chloro-

Catalog No.:AG0005S5 MDL No.:MFCD13188881

MF:C6H5ClN2O2 MW:172.5691

CAS No. 1018678-39-1

3-Pyridinecarboxylic acid, 4-chloro-2-(trifluoromethyl)-

Catalog No.:AG0005S4 MDL No.:MFCD22546902

MF:C7H3ClF3NO2 MW:225.5524

CAS No. 1018678-48-2

Benzoic acid, 2-(difluoromethyl)-, methyl ester

Catalog No.:AG0005S3 MDL No.:MFCD16140192

MF:C9H8F2O2 MW:186.1554

CAS No. 1018678-50-6

Benzaldehyde, 2-(difluoromethyl)-

Catalog No.:AG0005S2 MDL No.:MFCD16875639

MF:C8H6F2O MW:156.1294

CAS No. 1018679-79-2

1H-Pyrazolo[3,4-g]isoquinoline, 4a-(ethoxymethyl)-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-6-[[4-(trifluoromethyl)phenyl]sulfonyl]-, (4aR)-

Catalog No.:AG0005SV MDL No.:

MF:C26H25F4N3O3S MW:535.5536

CAS No. 101868-30-8

Benzoic acid, 3,5-dibromo-2-hydroxy-, 2-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylene]hydrazide

Catalog No.:AG0005T8 MDL No.:

MF:C19H16Br2N4O3 MW:508.1633

CAS No. 101868-36-4

Pyridine, 2-chloro-4,6-dimethyl-3,5-diphenyl-

Catalog No.:AG0005T7 MDL No.:

MF:C19H16ClN MW:293.7900

CAS No. 101868-79-5

9H-Carbazol-3-amine, N-(phenylmethyl)-

Catalog No.:AG0005T6 MDL No.:

MF:C19H16N2 MW:272.3437

CAS No. 1018680-09-5

Boronic acid, B-[5-(dimethylamino)-3-pyridinyl]-

Catalog No.:AG0005SU MDL No.:MFCD12964565

MF:C7H11BN2O2 MW:165.9854

CAS No. 1018680-22-2

Ethanone, 1-(3-amino-1-piperidinyl)-

Catalog No.:AG0005ST MDL No.:MFCD09264572

MF:C7H14N2O MW:142.1989

CAS No. 1018681-31-6

Benzene, 1-bromo-4-[(cyclopropylmethoxy)methyl]-

Catalog No.:AG0005SS MDL No.:MFCD14687047

MF:C11H13BrO MW:241.1243

CAS No. 101869-74-3

Cyclohexanemethanol, 4-methoxy-

Catalog No.:AG0005T5 MDL No.:MFCD26885663

MF:C8H16O2 MW:144.2114

CAS No. 101869-82-3

2-Propenoic acid, 3-(2,5-dichlorophenyl)-

Catalog No.:AG0005T4 MDL No.:MFCD03002786

MF:C9H6Cl2O2 MW:217.0487

CAS No. 1018690-17-9

Benzenecarbothioic acid, 2,5-difluoro-, hydrazide, hydrochloride (1:1)

Catalog No.:AG0005SR MDL No.:

MF:C7H7ClF2N2S MW:224.6587

CAS No. 10187-21-0

2,5-Pyrrolidinedione, 1-(4-hydroxyphenyl)-

Catalog No.:AG0005TF MDL No.:MFCD00466649

MF:C10H9NO3 MW:191.1834

CAS No. 10187-79-8

Acetamide, N-[1-methyl-3-(5-nitro-2-furanyl)-1H-1,2,4-triazol-5-yl]-

Catalog No.:AG0005TE MDL No.:

MF:C9H9N5O4 MW:251.1989

CAS No. 10187-80-1

Acetamide, N-[4-methyl-5-(5-nitro-2-furanyl)-4H-1,2,4-triazol-3-yl]-

Catalog No.:AG0005TD MDL No.:

MF:C9H9N5O4 MW:251.1989

CAS No. 10187-84-5

1H-1,2,4-Triazol-5-amine, N-methyl-3-(5-nitro-2-furanyl)-

Catalog No.:AG0005TC MDL No.:

MF:C7H7N5O3 MW:209.1622

CAS No. 10187-86-7

4H-1,2,4-Triazol-3-amine, 4-methyl-5-(5-nitro-2-furanyl)-

Catalog No.:AG0005TB MDL No.:

MF:C7H7N5O3 MW:209.1622

CAS No. 10187-89-0

1H-1,2,4-Triazol-5-amine, N-ethyl-3-(5-nitro-2-furanyl)-

Catalog No.:AG0005TA MDL No.:

MF:C8H9N5O3 MW:223.1888

CAS No. 10187-90-3

1H-1,2,4-Triazol-5-amine, 3-(5-nitro-2-furanyl)-N-propyl-

Catalog No.:AG0005T9 MDL No.:

MF:C9H11N5O3 MW:237.2153

CAS No. 101870-02-4

1,3,5-Triazine, 2,4-dichloro-6-(2-nitrophenoxy)-

Catalog No.:AG0005T3 MDL No.:MFCD18025182

MF:C9H4Cl2N4O3 MW:287.0591

CAS No. 101870-10-4

1H-Indole-6-carboxylic acid, 2,3-dihydro-2,3-dioxo-

Catalog No.:AG0005T2 MDL No.:MFCD17676217

MF:C9H5NO4 MW:191.1403

CAS No. 101870-22-8

Pyridine, 2-propoxy-

Catalog No.:AG0005T1 MDL No.:

MF:C8H11NO MW:137.1790

CAS No. 101870-58-0

8-Quinolinol, 2,5,7-trichloro-

Catalog No.:AG0005T0 MDL No.:MFCD00552678

MF:C9H4Cl3NO MW:248.4932

CAS No. 101870-60-4

Quinoline, 3-bromo-2-chloro-

Catalog No.:AG0005SZ MDL No.:MFCD08457743

MF:C9H5BrClN MW:242.4997

CAS No. 101870-78-4

3-Pyridinol, 6-(1-methylethyl)-

Catalog No.:AG0005SY MDL No.:MFCD10000595

MF:C8H11NO MW:137.1790

CAS No. 101871-32-3

Butanoic acid, 4-(butylamino)-4-oxo-, methyl ester

Catalog No.:AG0005SX MDL No.:

MF:C9H17NO3 MW:187.2362

CAS No. 101871-81-2

Urea, N-phenyl-N'-2-propyn-1-yl-

Catalog No.:AG0005SW MDL No.:MFCD11756585

MF:C10H10N2O MW:174.1992

CAS No. 1018828-72-2

IMidazo[1,2-a]pyridine-2-carboxylic acid, 8-(trifluoroMethyl)-

Catalog No.:AG0005TG MDL No.:

MF:C9H5F3N2O2 MW:230.1434

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