ABSTRACT
A facile strategy for the annulation of 2,6-dicyanoaniline moiety to steroidal A/B-ring is described from base catalyzed and microwave-promoted reaction of steroidal 3-keto-2-hydroxymethylenes with malononitrile in high yields. The generality of the reaction has been extended to non-steroidal cyclic and aliphatic ketohydroxylmethylenes.
Subject(s)
Aniline Compounds/chemistry , Microwaves , Steroids/chemistry , Molecular Structure , Steroids/chemical synthesisABSTRACT
The preparation of ring-A fused pyrimidines at the steroidal 2,3-position is herein described. The novel steroidal pyrimidines were prepared from the solid phase three-component reaction of 2-hydroxymethylene-3-keto steroids, arylaldehydes and ammonium acetate under microwave irradiation.
Subject(s)
Microwaves , Pyrimidines/chemistry , Steroids/chemical synthesis , Acetates/chemistry , Aldehydes/chemistry , Ketosteroids/chemistry , Steroids/chemistryABSTRACT
A facile strategy for the preparation of A-ring fused pyridosteroids has been accomplished in high yields by the reaction of Vilsmeier reagent (chloromethyleneiminium salt) with steroidal A-ring enamides (2- and 3-ene) under thermal conditions. The structure of 6'-chloro-5alpha-cholest [3,2-b]pyridine was determined by X-ray analysis.
Subject(s)
Chemistry, Organic/methods , Pyridines/chemistry , Pyridines/chemical synthesis , Steroids/chemistry , Steroids/chemical synthesis , Anaerobiosis , Crystallography, X-Ray , Hot Temperature , Molecular ConformationABSTRACT
The preparation of ring-A fused steroidal dehydropiperazine at the 3,4-position is herein described. The novel steroidal dehydropiperazines were prepared from the annulation reaction of ethylenediamine with 3-keto-4-en steroids in a one-pot reaction under microwave irradiation. The key step involves base catalysed aerial oxidation of the C-6 methylene group followed by cyclocondensation of ethylenediamine via Michael addition reaction.
