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Issue 7, 2020
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1,6-Addition of vinyl p-quinone methides with cyclic sulfamidate imines: access to 4-hydroxyaryl-2,6-diarylpyridines

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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

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Article information


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

Org. Biomol. Chem., 2020,18, 1337-1342
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, 18, 1337
DOI: 10.1039/C9OB02708D

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