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Synthesis of Benzo[4,5]imidazo[1,2-c]pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C-N Coupling and Cyclization.

ABSTRACT: 2-(2-Bromovinyl)benzimidazoles and 2-(2-bromophenyl)benzimidazoles react with cyanamide by microwave irradiation in dimethylformamide in the presence of a catalytic amount of CuI along with a base to give the corresponding benzo[4,5]imidazo[1,2-c]pyrimidin-1-amines and benzo[4,5]imidazo[1,2-c]quinazolin-6-amines, respectively, in moderate to good yields. 2-(2-Bromophenyl)indoles also react with cyanamide under similar conditions to afford indolo[1,2-c]quinazolin-6-amines. The reaction pathway seems to proceed via a sequence such as intermolecular C-N coupling, C-N formative cyclization, and tautomerization.

SUBMITTER: Dao PDQ

PROVIDER: S-EPMC6640920 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Synthesis of Benzo[4,5]imidazo[1,2-c]pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C-N Coupling and Cyclization.

Dao Pham Duy Quang PDQ Lee Ha Kyeong HK Sohn Ho-Sang HS Yoon Nam Sik NS Cho Chan Sik CS

ACS omega 20170626 6

2-(2-Bromovinyl)benzimidazoles and 2-(2-bromophenyl)benzimidazoles react with cyanamide by microwave irradiation in dimethylformamide in the presence of a catalytic amount of CuI along with a base to give the corresponding benzo[4,5]imidazo[1,2-c]pyrimidin-1-amines and benzo[4,5]imidazo[1,2-c]quinazolin-6-amines, respectively, in moderate to good yields. 2-(2-Bromophenyl)indoles also react with cyanamide under similar conditions to afford indolo[1,2-c]quinazolin-6-amines. Th ...[more]

PMID: 31457630

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