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Synthesis of Pyrimidine- and Quinazoline-Fused Benzimidazole-4,7-diones Using Combinatorial Cyclocondensation and Oxidation.

ABSTRACT: ?-Bromo-?,?-unsaturated aldehydes and 2-bromobenzaldehydes react with 4,7-dimethoxy-1H-benzo[d]imidazole-2-amine by microwave irradiation in dimethylformamide in the presence of a base to give the corresponding dimethoxy-substituted benzo[4,5]imidazo[1,2-a]pyrimidines and benzo[4,5]imidazo[1,2-a]quinazolines, respectively, in moderate to good yields. Oxidation of such N-fused hybrid scaffolds by aqueous ceric ammonium nitrate affords pyrimidine- and quinazoline-fused benzimidazole-4,7-diones in high yields.

SUBMITTER: Kim DY

PROVIDER: S-EPMC6643376 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Synthesis of Pyrimidine- and Quinazoline-Fused Benzimidazole-4,7-diones Using Combinatorial Cyclocondensation and Oxidation.

Kim Dong Young DY Quang Dao Pham Duy PD Cho Chan Sik CS

ACS omega 20181217 12

β-Bromo-α,β-unsaturated aldehydes and 2-bromobenzaldehydes react with 4,7-dimethoxy-1H-benzo[d]imidazole-2-amine by microwave irradiation in dimethylformamide in the presence of a base to give the corresponding dimethoxy-substituted benzo[4,5]imidazo[1,2-a]pyrimidines and benzo[4,5]imidazo[1,2-a]quinazolines, respectively, in moderate to good yields. Oxidation of such N-fused hybrid scaffolds by aqueous ceric ammonium nitrate affords pyrimidine- and quinazoline-fused ...[more]

PMID: 31458351

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