Synthesis of functionalized 1,4-dihydropyridines containing benzosultams catalyzed by lipase

As a base structural unit, 1,4-dihydropyridines (DHPs) containing benzosultams widely exist in bioactive molecules and drugs. These compounds are generally synthesized by organic-base catalyzed methods that require specifically functionalized substrates or harsh conditions. Herein, a [3+3] annulation reaction of cyclic N-sulfonyl ketimine with various substituted isatylidene malononitrile or benzylidene malononitriles was documented. This biocatalytic strategy provides a green route for synthesis of 1,4-DHPs containing benzosultams, with good functional groups compatibility and yields. Under optimal conditions, lipase leads to the formation of 1,4-DHPs containing benzosultams in up to 87% yield.

Automated summary

1,4-Dihydropyridines (DHPs) containing benzosultams are widely present in bioactive molecules and drugs as base structural units. These compounds are usually synthesized by organic-base catalyzed methods that require specifically functionalized substrates or harsh conditions. In this study, a [3+3] annulation reaction of cyclic N-sulfonyl ketimine with various substituted isatylidene malononitrile or benzylidene malononitriles was reported. This biocatalytic strategy provides a green route for the synthesis of 1,4-DHPs containing benzosultams, with good functional groups compatibility and yields. Under optimal conditions, lipase leads to the formation of 1,4-DHPs containing benzosultams in up to 87% yield.