THERMAL TRANSFORMATIONS OF 7-ARYL-1,6-DIAZABICYCLO[4.10]HEPTANES AND 6,13-DIARYLPERHYDRODIPYRIDAZINO[1,2-<i>a</i>:1',2'-<i>d</i>]-1,2,4,5-TETRAZINES

Authors

  • Ю. Б. Коптелов St. Petersburg State University, St. Petersburg 198504
  • А. И. Уколов St. Petersburg State University, St. Petersburg 198504

DOI:

https://doi.org/10.1007/7122

Keywords:

azomethineimine, N-arylmaleimide, 1, 6-diazabicyclo[4.1.0]heptane, tetrazine, 3-dipolar cycloaddition

Abstract

The thermolysis of 7-aryl-1,6-diazabicyclo[4.1.0]heptanes in the absence of 1,3-dipolarophiles leads to dimers of the initially formed azomethineimines, namely, 6,13-diaryloctahydrodipyridazino[1,2-a:1',2'-d]-1,2,4,5-tetrazines The thermolysis of such diaziridines in the presence of N-arylmaleimides leads predominantly to the trans cycloaddition adducts. The trans adducts are the only products of the thermolysis in the presence of 2,6-disubstituted N-phenylmaleimides. The cis adducts predominated in the thermolysis of 6,13-diaryloctahydrodipyridazino[1,2-a:1',2'-d]-1,2,4,5-tetrazines  in the presence of N-arylmaleimides without substituents in the ortho position of the benzene ring.

How to Cite
Koptelov, Yu. B.; Ukolov, A. I. Chem. Heterocycl. Compd. 2008, 44, 852. [Khim. Geterotsikl. Soedin. 2008, 1062.]

For this article in the English edition see DOI 10.1007/s10593-008-0120-7

 

Published

2022-10-07

Issue

Section

Original Papers