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A distal vinyl shift (DVS) through quadruple domino reaction: synthesis of N-vinyl benzoheterocyclic scaffolds.

ABSTRACT: A conceptually novel Distal Vinyl Shift (DVS) through quadruple domino reaction involving imine formation, oxazole/thiazole/oxazine formation, aza-Michael addition and selective retro oxa/aza-Michael addition leading towards N-vinyl benzoxazoles/benzothiazoles/N-vinyl 1,3-benzoxazines has been developed for the first time. This reaction is highly stereoselective and was carried out efficiently without using any catalyst as well as column chromatography purification with wide substrate scope in very good to excellent yields.

SUBMITTER: Bakthadoss M

PROVIDER: S-EPMC9079281 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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A distal vinyl shift (DVS) through quadruple domino reaction: synthesis of N-vinyl benzoheterocyclic scaffolds.

Bakthadoss Manickam M Mushaf Mohammad M

RSC advances 20180328 22

A conceptually novel Distal Vinyl Shift (DVS) through quadruple domino reaction involving imine formation, oxazole/thiazole/oxazine formation, aza-Michael addition and selective retro oxa/aza-Michael addition leading towards N-vinyl benzoxazoles/benzothiazoles/N-vinyl 1,3-benzoxazines has been developed for the first time. This reaction is highly stereoselective and was carried out efficiently without using any catalyst as well as column chromatography purification with wide substr ...[more]

PMID: 35539421

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