Reaction of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes with Aryl Isocyanates and Aryl Isothiocyanates

Alexander P. Molchanov; Denis I. Sipkin; Yuri B. Koptelov; Rafael R. Kostikov

doi:10.1055/s-2000-8690

Synlett 2000; 2000(12): 1779-1780
DOI: 10.1055/s-2000-8690

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Reaction of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes with Aryl Isocyanates and Aryl Isothiocyanates

Alexander P. Molchanov^* , Denis I. Sipkin, Yuri B. Koptelov, Rafael R. Kostikov

^*Department of Organic Chemistry, St. Petersburg State University, Universitetskii pr. 2, 198904 St. Petersburg, Russia; Fax 7-812-4 28 69 39; E-mail: rkost@rk1198.spb.edu

Abstract

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Heating 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of aryl isocyanates or aryl isothiocyanates leads to the formation of the corresponding 2,3-diarylperhydropyrazolo[1,2-a][1,2,4]triazol-1-one or 2,3-diarylperhydropyrazolo[1,2-a][1,2,4]triazol-1-thione in good yield as a result of 1,3-dipolar cycloaddition of isocyanate (isothiocyanate) to an initially formed ylide.

diaziridine heterocycles - 1,3-dipolar cycloadditions - nitrogen ylides - isocyanates - isothiocyanates

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