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

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 devel...

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Detalles Bibliográficos
Autores principales: Bakthadoss, Manickam, Mushaf, Mohammad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9079281/
https://www.ncbi.nlm.nih.gov/pubmed/35539421
http://dx.doi.org/10.1039/c8ra01478g
Descripción
Sumario: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.