Issue 17, 2020

Base-promoted 1,6-conjugate addition of alkylazaarenes to para-quinone methides

Abstract

1,1,2-Triarylethanes embedded with an azaarene unit were prepared in a single step at ambient temperature via the sodium hexamethyldisilazide mediated 1,6-conjugate addition of unactivated alkylazaarenes on para-quinone methides (p-QMs). The extent of this methodology was investigated with a wide range of p-QMs and alkylazaarenes, and the respective products were obtained in moderate to excellent yields. The regioselective 1,6-conjugate addition of the trialkylazaarene precursor on para-quinone methide was also presented. Besides, we showcased the direct synthesis of the 1,1,2-triarylethane derivative from aldehyde via the in situ generation of para-quinone methide.

Graphical abstract: Base-promoted 1,6-conjugate addition of alkylazaarenes to para-quinone methides

Supplementary files

Article information

Article type
Paper
Submitted
26 Feb 2020
Accepted
08 Apr 2020
First published
08 Apr 2020

Org. Biomol. Chem., 2020,18, 3354-3359

Base-promoted 1,6-conjugate addition of alkylazaarenes to para-quinone methides

A. Rayaroth, R. K. Singh, K. A. V., K. Hari and A. Kaliyamoorthy, Org. Biomol. Chem., 2020, 18, 3354 DOI: 10.1039/D0OB00419G

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