The reaction of (2-oxo-2-phenyl-ethyl sulfanyl)-Acetic Acid with Chalcones: Double Michael Addition-Aldol Reaction Formation of Unexpected (5-Benzoyl-2-hydroxy-2,4-6-triphenyl-cyclohexyl) -phenyl-methanone-Reference-Cited by-同舟云学术

The reaction of (2-oxo-2-phenyl-ethyl sulfanyl)-Acetic Acid with Chalcones: Double Michael Addition-Aldol Reaction Formation of Unexpected (5-Benzoyl-2-hydroxy-2,4-6-triphenyl-cyclohexyl) -phenyl-methanone

Published:2022-10-31 Issue:5 Volume:38 Page:1250-1254
ISSN:2231-5039
Container-title:Oriental Journal Of Chemistry
language:en
Short-container-title:Orient. J. Chem

Author:

Suriyakala Tevaraj¹^ORCID,Ravindran Gurusamy¹^ORCID

Affiliation:

1. Department of Chemistry, Cardamom Planters’ Association College, Bodinayakanur – 625513. Madurai Kamaraj University, Madurai. Tamil Nadu. India.

Abstract

A greener approach one-pot reaction of (2-oxo-2-phenyl-ethyl sulfanyl)-acetic acid with chalcones in presence of a base to afford an unexpected (5-Benzoyl-2-hydroxy-2,4-6-triphenyl-cyclohexyl) – phenyl-methanone product. The reaction proceeds via sequential double Michael addition-aldol reaction mediated three consecutive C-C bonds are formed in one pot. The procedure has a short reaction time, easy workup, and moderate yield of products. The structure of all synthesized compounds was determined by using 1HNMR and 13CNMR Spectral analysis.

Publisher

Oriental Scientific Publishing Company

Subject

Drug Discovery,Environmental Chemistry,Biochemistry,General Chemistry

Reference20 articles.

1. 1. a) Gawley. R.E. Synthesis, 1976, 777. (b) Jung, M.E. Tetrahedron,1976, 32,3. (c) Peters, J.A Synthesis, 1979, 321.

2. 2. Jung, M.E. Comprehensive organic synthesis (eds), 1993. B.M. Trost and Fleming (Oxford: Pergamon Press) vol.4, p. 1-68.

3. 3. Bergmann. E.D,; Ginsburg, D,; Pappo, R, Organic React., 1959, 10, 179.

4. 4. (a) Ranu, B,C.; Bhar, S.; Tetrahedron,1992,48, 1342. (b).Ranu, B.C.;Bhar, S.; Sarkar, D.C. Tetrahedron Lett., 1991, 32, 2811.

5. 5. Romanova, N.N.; Gravis, A.G.; Sharidullina, G.M.; Leshcheva, I.F.; Bundle, Y.G. Mendeleev Commun., 1997, 213.