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Intramolekulare 1,3-dipolare Cycloadditionen von Diarylnitriliminen aus 2,5-Diaryltetrazolen


Meier, Hansruedi; Heimgartner, Heinz (1985). Intramolekulare 1,3-dipolare Cycloadditionen von Diarylnitriliminen aus 2,5-Diaryltetrazolen. Helvetica Chimica Acta, 68(5):1283-1300.

Abstract

Alkenyl-substituted diaryl-nitrile-imines - generated by photolysis or thermolysis of alkenyl-substituted 2,5-diaryl-tetrazoles - undergo a regioselective intramolecular [2+3] cycloaddition to yield new heterocyclic compounds, e.g. fused 2-pyrazolines. With alkinyl derivatives, the corresponding pyrazoles have been formed. UV evidence is given for the intermediate nitrile-imine at - 190°. The latter can be trapped using an excess of carboxylic acid (UV evidence for a new intermediate at - 120°). In this case, the corresponding rearranged addition product N'-acyl-N'-aryl-benzohydrazide is isolated in good yield.

Alkenyl-substituted diaryl-nitrile-imines - generated by photolysis or thermolysis of alkenyl-substituted 2,5-diaryl-tetrazoles - undergo a regioselective intramolecular [2+3] cycloaddition to yield new heterocyclic compounds, e.g. fused 2-pyrazolines. With alkinyl derivatives, the corresponding pyrazoles have been formed. UV evidence is given for the intermediate nitrile-imine at - 190°. The latter can be trapped using an excess of carboxylic acid (UV evidence for a new intermediate at - 120°). In this case, the corresponding rearranged addition product N'-acyl-N'-aryl-benzohydrazide is isolated in good yield.

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Additional indexing

Other titles:Intramolecular 1,3-Dipolar Cycloadditions of Diaryl-nitrile-imines Generated from 2,5-Diaryl-tetrazoles
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1985
Deposited On:16 Jun 2014 11:17
Last Modified:05 Apr 2016 17:55
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19850680524
Permanent URL: https://doi.org/10.5167/uzh-96605

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