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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

12 Issues per year


IMPACT FACTOR 2016: 0.631

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1865-7117
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Volume 56, Issue 11

Issues

Einige Umsetzungen von Inhydrazinen mit Isocyanaten: [2+2]- und [4+2]Cycloadditionen, (Hydrazinoethinyl)metallierung / Some Reactions of Ynehydrazines with Isocyanates: [2+2]- and [4+2]Cycloadditions, (Hydrazinoethynyl)metallation

Gerhard Himbert
  • Corresponding author
  • Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-67663 Kaiserslautern, Germany
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/ Oliver Gerulat
  • Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-67663 Kaiserslautern, Germany
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Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-2001-1115

The (silylethynyl)- and the (tolylethinyl)-hydrazines 1a and 1b react with aryl isocyanates 2a-e and arylsulfonyl isocyanates 2f,g to form the corresponding substituted 3-arylimino-(or arylsulfonylimino-) 1,1,2-trimethyl-5-oxopyrazolidinium-4-ides 3a-h. The silyl group in the 4-position can be replaced by a hydrogen atom (formation of 6a-e). Heating of 6d in toluene induced the unequivocal transformation of the betaine to an isomer, the spectrocopic data of which are in concordance with those of the 4-quinolone derivative 7. Aroyl isocyanates 8 react in a [4+2]cycloaddition with la to furnish the 1,3-oxazin-4-ones 9a and b. The stannylated ynehydrazine 1c adds the cumulenic system of an aryl isocyanate (2d) across the Csp-Sn single bond, and trimethylstannyl .N-(p-chlorophenyl)-3-(trimethylhydrazino)propiolimidate 10 is isolated. With two molecules of 2d the hydantoin derivative 11 is formed.

Keywords: Cycloadditions; Cyclic Betaines; l,3-Oxazin-4-ones

About the article

Received: 2001-08-02

Published Online: 2014-06-02

Published in Print: 2001-11-01


Citation Information: Zeitschrift für Naturforschung B, Volume 56, Issue 11, Pages 1196–1204, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2001-1115.

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