5,5'-双(1,2,3-二噻唑基)的转化为异噻唑并[5,4-b]异噻唑。
The Conversion of 5,5'-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-]isothiazoles.
机构信息
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia.
Nanotechnology Education and Research Center, South Ural State University, Chelyabinsk 454080, Russia.
出版信息
Molecules. 2018 May 24;23(6):1257. doi: 10.3390/molecules23061257.
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-]-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.
4,4'-二氯-、4,4'-二芳基-和 4,4'-二(噻吩-2-基)-5,5'-双(1,2,3-二噻唑啉)的热解提供了相应的 3,6-二氯-、3,6-二芳基和 3,6-二(噻吩-2-基)异噻唑并[5,4-]-异噻唑，产率从低到高。在亲硫试剂三苯基膦或四乙基碘化铵的存在下，4,4'-二芳基-和 4,4'-二(噻吩-2-基)-5,5'-双(1,2,3-二噻唑啉)的转化在较低温度下发生。提出了优化的反应条件和用于亲硫介导的环转化的机理。
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