4,4-DIMETHYL-4,5-DIHYDRO-1,2-DITHIOLO[3,4-<i>c</i>]QUINOLINE-1-THIONES IN 1,3-DIPOLAR CYCLOADDITION REACTIONS WITH ACETYLENIC DIPOLAROPHILES

Abstract

The behavior of 4,4-dimethyl-4,5-dihydro-1,2-dithiolo[3,4-c]quinoline-1-thiones in the 1,3-dipolar cycloaddition reaction with acetylenic dipolarophiles has been studied. The rate of cycloaddition is reduced along with the decrease of electron-deficiency of the triple bond. Substituted 4-(1',3'-dithiol-2'-ylidene)-1,2-dihydroquinoline-3-thiones were shown to be the reaction products. On using a twofold excess of acetylenedicarboxylic acid dimethyl ester, adducts of composition 1 : 2 were formed which occured to be substituted 1',3'-dithiole-2'-spiro-1-(5,6-dihydrothiino[2,3-c]quinolines).

Authors: Kh. S. Shikhaliev, S. M. Medvedeva, G. I. Ermolova, and G. V. Shatalov.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (5), pp 587-591

http://link.springer.com/article/10.1007/BF02324643