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Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes.

ABSTRACT: N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of ?,?-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable ?,?-diEWG cyclic vinylogous amides for the efficient synthesis of bicyclic N-unprotected lactams similar to those in many useful drugs.

SUBMITTER: Dzieszkowski K

PROVIDER: S-EPMC7590975 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes.

Dzieszkowski Krzysztof K Barańska Izabela I Rafiński Zbigniew Z

The Journal of organic chemistry 20200429 10

N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable α,β-diEWG cyclic vinylogous amides for the efficient synthesis of bicyclic N-unprotected lactams similar to those in many useful drugs. ...[more]

PMID: 32312044

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