1. The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
- Author
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Konstantinova, Lidia S., Baranovsky, Ilia V., Strunyasheva, Vlada V., Kalogirou, Andreas S., Popov, Vadim V., Lyssenko, Konstantin A., Koutentis, Panayiotis A., Rakitin, Oleg A., Kalogirou, Andreas S. [0000-0002-5476-5805], and Koutentis, Panayiotis A. [0000-0002-4652-7567]
- Subjects
Models, Molecular ,Tetraethylammonium iodide ,isothiazoles ,ring transformation ,Pharmaceutical Science ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Medicinal chemistry ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,sulfur-nitrogen heterocycles ,Drug Discovery ,dithiazoles ,Physical and Theoretical Chemistry ,Triphenylphosphine ,Reaction conditions ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Thermal decomposition ,Temperature ,0104 chemical sciences ,Thiazoles ,chemistry ,Chemistry (miscellaneous) ,Molecular Medicine - Abstract
Thermolysis of 4,4&prime -dichloro-, 4,4&prime -diaryl-, and 4,4&prime -di(thien-2-yl)-5,5&prime -bi(1,2,3-dithiazol-ylidenes) affords the respective 3,6-dichloro-, 3,6-diaryl- and 3,6-di(thien-2-yl)isothiazolo[5,4-d]-isothiazoles in low to high yields. The transformation of the 4,4&prime -diaryl- and 4,4&prime -di(thien-2-yl)-5,5&prime -bi(1,2,3-dithiazolylidenes) occurs at lower temperatures in the presence of the thiophiles triphenylphosphine or tetraethylammonium iodide. Optimized reaction conditions and a mechanistic rationale for the thiophile-mediated ring transformation are presented. 23 6
- Published
- 2018
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