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Base-promoted highly efficient synthesis of nitrile-substituted cyclopropanes via Michael-initiated ring closure.

ABSTRACT: A convenient and efficient annulation reaction has been developed for the general synthesis of dinitrile-substituted cyclopropanes in moderate to excellent yields. A variety of 2-arylacetonitriles and α-bromoennitriles were compatible under the standard conditions. The reaction was achieved through tandem Michael-type addition followed by intramolecular cyclization. The preliminary application of this method was confirmed by the synthesis of the 2,4-dioxo-3-azabicyclo[3.1.0]hexane scaffold.

SUBMITTER: Ye M

PROVIDER: S-EPMC9536251 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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Base-promoted highly efficient synthesis of nitrile-substituted cyclopropanes <i>via</i> Michael-initiated ring closure.

Ye Min M Xu Fan F Bai Yun Y Zhang Fanglian F Wang Wenjia W Qian Yiping Y Chen Zhengwang Z

RSC advances 20221006 44

A convenient and efficient annulation reaction has been developed for the general synthesis of dinitrile-substituted cyclopropanes in moderate to excellent yields. A variety of 2-arylacetonitriles and α-bromoennitriles were compatible under the standard conditions. The reaction was achieved through tandem Michael-type addition followed by intramolecular cyclization. The preliminary application of this method was confirmed by the synthesis of the 2,4-dioxo-3-azabicyclo[3.1.0]hexane scaffold. ...[more]

PMID: 36320497

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