The Fischer-indole cyclization of phenylhydrazones and N-methylphenylhydrazones of some 6-substituted cholestan-3-ones
1972; Elsevier BV; Volume: 28; Issue: 9 Linguagem: Inglês
10.1016/0040-4020(72)80084-x
ISSN1464-5416
Autores Tópico(s)Organic Chemistry Cycloaddition Reactions
ResumoThe Fischer-indole cyclization of the phenylhydrazones and N-methylphenylhydrazones of 5α- and 5β-cholestan-3-one has been reinvestigated, and additional products characterized. The Fischer-indole cyclization of the phenylhydrazones and N-methylphenylhydrazones of certain 6-substituted cholestan-3-ones was also investigated. Derivatives of cholest-2-eno[3,2-b]indole were the major products of the reaction of 5α- and 5β-cholestane-3,6-dione, although in the latter case, cyclization also occurred to give the cholest-3-eno[3,4-b]indole system. 6-Substituted cholest-3-eno[3,4-b]indole derivatives were obtained in good yield by the cyclization of the N-methylphenylhydrazones of 6β-acetoxy- and 6β-hydroxy-5β-cholestan-3-one.
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