Jump to main content
Jump to site search


1,6-Addition of vinyl p-quinone methides with cyclic sulfamidate imines: access to 4-hydroxyaryl-2,6-diarylpyridines

Author affiliations

Abstract

A simple and powerful one-pot regioselective 1,6-addition elimination–6π-aza-electrocyclization–aromatization reaction of vinyl/dienyl-substituted para-quinone methides with a bunch of cyclic sulfamidate imines as 2C1N synthons promoted by DABCO as a solid organobase in an open atmosphere is reported for the first time. The above-mentioned C–C and C–N bond formation process provides good to high yields of a wide range of symmetrically and unsymmetrically 2,4,6-trisubstituted pyridines possessing a sterically hindered phenolic moiety at the C4-position with a broad substrate scope. This domino [3 + 3] cyclization reaction gives rise to several compatible functionalities under metal-free conditions. Finally, the large-scale synthesis of pyridine derivatives has been demonstrated.

Graphical abstract: 1,6-Addition of vinyl p-quinone methides with cyclic sulfamidate imines: access to 4-hydroxyaryl-2,6-diarylpyridines

Back to tab navigation

Supplementary files

Article information


Submitted
20 Dec 2019
Accepted
15 Jan 2020
First published
16 Jan 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

1,6-Addition of vinyl p-quinone methides with cyclic sulfamidate imines: access to 4-hydroxyaryl-2,6-diarylpyridines

S. Guin, S. K. Gudimella and S. Samanta, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02708D

Social activity

Search articles by author

Spotlight

Advertisements