Preparative conversion of chloralamides to 2,5‐diaryl‐3a,6a‐dihydro‐[1,3]thiazolo[4,5‐<i>d</i>][1,3]thiazoles with the Lawesson reagent

Demydchuk, Bogdan A.; Броварец, В. С.; Василенко, А. Н.; Drach, B. S.

doi:10.1002/hc.20493

Cited by 3 publications

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“…Since the first thiazolo[5,4- d ]thiazole ( 1 ) was reported in 1960 [4], over 400 analogues have been made and many were incorporated into dyes, oligomers and polymers for semiconductors and plastic electronics [5,6]. Interestingly, the isomeric thiazolo[4,5- d ]thiazole ( 2 ) which, like thiazolo[5,4- d ]thiazole ( 1 ), shares a common C-C bond between the two thiazoles is less well known; only 14 analogues are known [7,8,9,10,11,12,13]. Despite this, several analogues have useful properties as plant fungacides [10], antitumour agents [7], and as non-linear optical materials [8].…”

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confidence: 99%

The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles

et al. 2018

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Thermolysis of 4,4′-dichloro-, 4,4′-diaryl-, and 4,4′-di(thien-2-yl)-5,5′-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′-diaryl- and 4,4′-di(thien-2-yl)-5,5′-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.

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