Synthesis 2017; 49(06): 1255-1263
DOI: 10.1055/s-0036-1588908
paper
© Georg Thieme Verlag Stuttgart · New York

Practical and Efficient Synthesis of Polyaryl(hetaryl)-Substituted Cyclohexenones and Salicylates

Valerii Z. Shirinian*a, Alexey M. Kavuna, b, Andrey G. Lvova, Igor V. Zavarzina, Michail M. Krayushkina
  • aN. D. Zelinsky Institute of Organic Chemistry, RAS 47, Leninsky prosp., 119991 Moscow, Russian Federation   Email: shir@ioc.ac.ru
  • bHigher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Moscow, Russian Federation
Further Information

Publication History

Received: 05 September 2016

Accepted after revision: 17 October 2016

Publication Date:
24 November 2016 (eFirst)

Abstract

A new efficient method was developed for the synthesis of triaryl-substituted cyclohexenones and salicylates. The method is based on the Robinson annulation of readily available keto esters and chalcones, followed by the aromatization of the cyclohexenone moiety. The aromatization can be accomplished either by reaction with bromine in boiling chloroform or bromination with copper(II) bromide in ethanol followed by treatment with pyridine or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The new synthetic method was also implemented in a one-pot protocol, which in some cases resulted in higher yields of the final product compared to those obtained in the stepwise synthesis.

Supporting Information