Annulation strategies for diverse heterocycles via the reductive transformation of 2-nitrostyrenes

Reduction of the stable nitro group is a fundamental and widely used transformation for the construction of complex and functionalized heterocyclic architectures. The unfolding of the reactivity of the nitro group in the 2-nitrostyrene moiety not only triggers the formation of carbon-nitrogen bonds, but also offers the opportunity for annulation and heteroannulation, thereby providing a cascade process for the synthesis of highly conjugated natural and unnatural molecules. In this review, we comprehensively discuss the use of 2-nitrostyrene motifs in the synthesis of various N-heterocycles. We offer readers an overview of the synthetic achievements achieved to date, highlighting their important features, reactivities, and mechanisms.

Automated summary

The reduction of the stable nitro group is a fundamental and widely used transformation for the construction of complex and functionalized heterocyclic architectures. The reactivity of the nitro group in the 2-nitrostyrene moiety not only triggers the formation of carbon-nitrogen bonds, but also offers the opportunity for annulation and heteroannulation, providing a cascade process for the synthesis of highly conjugated natural and unnatural molecules. This review comprehensively discusses the use of 2-nitrostyrene motifs in the synthesis of various N-heterocycles, highlighting their important features, reactivities, and mechanisms.