Synthesis of Aza Steroids of Cholestane Series

A. H. Siddiqui, K. Venkateshwer Rao, Mahmood Memariani and Vijaya Sen Reddy

Department of Chemistry, Nizam College, Hyderabad-500 001 India.

ABSTRACT:

The Beckmann rearrangement of 3 β - carbomethoxy oxy -7-oxo-5-cholestene-7-oxime (IIb) with p-toluene sulphonyl chloride/ pyridine or thionyl chloride afforded the lactam, 3 β -carbomethoxy oxy-7a-aza-7-oxo-B-homo-5α-cholestane (IIIa). The schmidt reaction of the ketone (IIa) using sodium azide and sulphuric acid furnishes the same lactam (IIIa). However, the schmidt reaction of the same ketone using hydrazoic acid and boron trifluoride etherate gave 3 β -carbomeethoxy oxy -en{7a,7-d] tetrazole (IV).

KEYWORDS:

Aza; Steroids; Cholestane

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Copy the following to cite this article: Siddiqui A. H, Rao K. V, Memariani M, Reddy V. S. Synthesis of Aza Steroids of Cholestane Series. Orient J Chem 1988;4(1).

Copy the following to cite this URL: Siddiqui A. H, Rao K. V, Memariani M, Reddy V. S. Synthesis of Aza Steroids of Cholestane Series. Orient J Chem 1988;4(1). Available from: http://www.orientjchem.org/?p=41740