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

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

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2017, Volume: 49, Number: 06, Pages: 1255-1263 Pages count : 9 DOI: 10.1055/s-0036-1588908

Authors

Shirinian Valerii Z. ¹ , Kavun Alexey M. ^2,1 , Lvov Andrey G. ¹ , Zavarzin Igor V. ¹ , Krayushkin Michail M. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, RAS 47, Leninsky prosp., 119991 Moscow, Russian Federation
2	Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Moscow, Russian Federation

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.

Shirinian V.Z. , Kavun A.M. , Lvov A.G. , Zavarzin I.V. , Krayushkin M.M.
Practical and Efficient Synthesis of Polyaryl(hetaryl)-Substituted Cyclohexenones and Salicylates
Synthesis-Stuttgart. 2017. V.49. N06. P.1255-1263. DOI: 10.1055/s-0036-1588908 WOS Scopus OpenAlex

Web of science:	WOS:000398095600012
Scopus:	2-s2.0-84997161511
OpenAlex:	W2551248583

DB	Citing
OpenAlex	9
Scopus	8
Web of science	7