THERMAL INDOLIZATION OF ARYLHYDRAZONES

THERMAL INDOLIZATION OF ARYLHYDRAZONES

Thermal cyclization of arylhydrazones in the absence of acid catalyst has been investigated. Indole was not obtained from acetaldehyde phenylhydrazone; aniline, N-ethylaniline, and an unidentified compound were isolated. Phenylhydrazones of cyclohexanone and cyclopentanone and their 2-substituted de...

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Veröffentlicht in:Canadian journal of chemistry 1965-01, Vol.43 (1), p.296-301
Hauptverfasser: Kelly, A. H, McLeod, D. H, Parrick, J
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container_title Canadian journal of chemistry
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creator Kelly, A. H
McLeod, D. H
Parrick, J
description Thermal cyclization of arylhydrazones in the absence of acid catalyst has been investigated. Indole was not obtained from acetaldehyde phenylhydrazone; aniline, N-ethylaniline, and an unidentified compound were isolated. Phenylhydrazones of cyclohexanone and cyclopentanone and their 2-substituted derivatives were cyclized, often in good yield, to the indole and indolenine; the nature of the substituent markedly influences the ratio of the two products. Gas-liquid chromatographic analysis of the reaction mixture from indolization of two arylhydrazones revealed no crossed products. Nitrophenylhydrazones do not cyclize in good yield, but thermal indolization of some pyridylhydrazones is a good method for the preparation of pyrrolopyridines.
doi_str_mv 10.1139/v65-033
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title THERMAL INDOLIZATION OF ARYLHYDRAZONES
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