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DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita-Baylis-Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives.

ABSTRACT: An intriguing DABCO-catalyzed and DBU-promoted one-pot synthesis of an important class of (2-hydroxyaryl)pyridine derivatives bearing a carboxylate or a nitrile group suitably placed at C3 position of the aza-ring has been achieved in acceptable chemical yields with a broad functional group tolerance. This sequential C-C/C-N bond making process proceeds through a regioselective allylic alkylation/aza-Michael reaction between MBH carbonates derived from an acrylate/acrylonitrile and N-sulfonyl ketimines as C,N-binucleophiles catalyzed by DABCO, followed by elimination of SO₂ under the influence of base and subsequent aromatization in an open atmosphere.

SUBMITTER: Guin S

PROVIDER: S-EPMC6244423 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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DABCO- and DBU-promoted one-pot reaction of <i>N</i>-sulfonyl ketimines with Morita-Baylis-Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives.

Guin Soumitra S Gupta Raman R Majee Debashis D Samanta Sampak S

Beilstein journal of organic chemistry 20181102

An intriguing DABCO-catalyzed and DBU-promoted one-pot synthesis of an important class of (2-hydroxyaryl)pyridine derivatives bearing a carboxylate or a nitrile group suitably placed at C3 position of the aza-ring has been achieved in acceptable chemical yields with a broad functional group tolerance. This sequential C-C/C-N bond making process proceeds through a regioselective allylic alkylation/aza-Michael reaction between MBH carbonates derived from an acrylate/acrylonitrile and <i>N</i>-sulf ...[more]

PMID: 30498526

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