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A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation/Ring-Expansion Approach to Substituted Azepanes.

ABSTRACT: Seven-membered nitrogen-containing heterocycles are considerably underrepresented in the literature compared to their five- and six-membered analogues. Herein, we report a relatively understudied photochemical rearrangement of N-vinylpyrrolidinones to azepin-4-ones in good yields. This transformation allows for the conversion of readily available pyrrolidinones and aldehydes to densely functionalized azepane derivatives in a facile two step procedure.

SUBMITTER: Thullen SM 

PROVIDER: S-EPMC5976449 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation/Ring-Expansion Approach to Substituted Azepanes.

Thullen Scott M SM   Rubush David M DM   Rovis Tomislav T  

Synlett : accounts and rapid communications in synthetic organic chemistry 20170629 20

Seven-membered nitrogen-containing heterocycles are considerably underrepresented in the literature compared to their five- and six-membered analogues. Herein, we report a relatively understudied photochemical rearrangement of N-vinylpyrrolidinones to azepin-4-ones in good yields. This transformation allows for the conversion of readily available pyrrolidinones and aldehydes to densely functionalized azepane derivatives in a facile two step procedure. ...[more]

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