THERMAL OPENING OF THE DIAZIRIDINE FRAGMENT IN 1-METHYL- AND 1,3,3-TRIMETHYL-1,3,4,8b-TETRAHYDRO[1,2]DIAZIRINO[3,1-<i>a</i>]ISOQUINOLINES IN THE PRESENCE OF N-ARYLMALEIMIDES
DOI:
https://doi.org/10.1007/7123Keywords:
azomethineimines, N-arylmaleimides, diaziridine, 3, 4-dihydroisoquinoline, 1, 3-dipolar cycloadditionAbstract
The thermal opening of the diaziridine ring in 1-methyl- and 1,3,3-trimethyl-1,3,4,8b-tetra-hydro[1,2]diazirino[3,1-a]isoquinolines in the presence of N-arylmaleimides leads to the predominant or exclusive formation of the trans isomers of the products of 1,3-dipolar cycloaddition. In the absence of dipolarophile, the conversion of the starting diaziridines is incomplete over the same time period,
while the thermolysis products are N-[3,4-dihydro-2(1H)-isoquinolyl]- and N-[3,3-dimethyl-3,4-di-hydro-2(1H)-isoquinolyl]-N-methyleneamines formed as the result of isomerization of intermediate labile azomethineimines.
How to Cite
Koptelov, Yu. B.; Saik, S. P.; Molchanov, A. P. Chem. Heterocycl. Compd. 2008, 44, 860. [Khim. Geterotsikl. Soedin. 2008, 1071.]
For this article in the English edition see DOI 10.1007/s10593-008-0122-5
