Bromination of steroidal 3-keto-4,6-diene-Reference-Cited by-同舟云学术

Bromination of steroidal 3-keto-4,6-diene

Published:2001-10 Issue:10 Volume:2001 Page:442-443
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Jaime Arelys¹,Reyes Mayra¹,Ruiz José A.¹,Vélez Hermán¹,Méndez José M.²,Suárez Margarita³

Affiliation:

1. Centro de Química Farmacéutica, Ave. 21 y 200, Atabey, P.O. Box 16042, Ciudad Habana, Cuba

2. Departamento de Química Orgánica, Facultad de Química, UNAM, México D.F., México

3. Laboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana, 10400-Ciudad Habana, Cuba

Abstract

The bromination reaction on 3-keto-4,6-diene steroids, via an epoxide intermediate, with hydrobromic acid in acetic acid medium gives the corresponding 6-bromo derivative. On the other hand, bromination with molecular bromine and subsequent dehydrobromination in an aprotic solvent and basic media afforded the unexpected 4-bromo derivative. In this work we suggest an alternative mechanism for explaining the bromine transposition from C6 to C4.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/030823401103168406

Reference9 articles.

1. ZeelenF.J. Medicinal Chemistry of Steroids, Elsevier Science Publishing Company. Inc. New York. 1990, Vol. 15, Chapter 9, p. 185.

2. Synthesis and biological activity of 17-esters of 6-dehydro-16-methylene-17.alpha.-hydroxyprogesterones

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1. ChemInform Abstract: Bromination of Steroidal 3-Keto-4,6-diene.;ChemInform;2010-05-22