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One-pot synthesis of 2-amino-indole-3-carboxamide and analogous.

ABSTRACT: An efficient one-pot, two-step solution-phase synthetic method was developed to synthesize twenty-three 2-amino-indole-3-carboxamides (3) from 2-halonitrobenzene (1) or heterocyclic analogous and cyanoacetamides (2). In this sequence, first, intermediate 2-cyano-2-(2-nitrophenyl)acetamide (4) was generated under basic condition via S(NAr) reaction; after direct addition of hydrochloric acid solution, FeCl(3), and Zn powder, indole 3 was generated via reduction/cyclization process.

SUBMITTER: Wang K

PROVIDER: S-EPMC3124116 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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One-pot synthesis of 2-amino-indole-3-carboxamide and analogous.

Wang Kan K Herdtweck Eberhardt E Dömling Alexander A

ACS combinatorial science 20101217 2

An efficient one-pot, two-step solution-phase synthetic method was developed to synthesize twenty-three 2-amino-indole-3-carboxamides (3) from 2-halonitrobenzene (1) or heterocyclic analogous and cyanoacetamides (2). In this sequence, first, intermediate 2-cyano-2-(2-nitrophenyl)acetamide (4) was generated under basic condition via S(NAr) reaction; after direct addition of hydrochloric acid solution, FeCl(3), and Zn powder, indole 3 was generated via reduction/cyclization process. ...[more]

PMID: 21395342

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