Department of Chemistry and Biology, Universität Siegen, Adolf-Reichwein-Straße, D-57068 Siegen, Germany.
Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität, Max-von-Laue-Straße 7, 60438 Frankfurt am Main, Germany.
Beilstein J Org Chem. 2014 Dec 15;10:2989-96. doi: 10.3762/bjoc.10.317. eCollection 2014.
A versatile synthetic procedure is described to prepare the benzimidazole-fused 1,2,4-thiadiazoles 2a-c via a methanesulfonyl chloride initiated multistep cyclization involving the intramolecular reaction of an in-situ generated carbodiimide with a thiourea unit. The structure of the intricate heterocycle 2a was confirmed by single-crystal X-ray analysis and its mechanism of formation supported by DFT computations.
描述了一种通用的合成方法,通过甲磺酰氯引发的多步环化反应,包括原位生成的碳二亚胺与硫脲单元的分子内反应,制备苯并咪唑稠合的 1,2,4-噻二唑 2a-c。复杂杂环 2a 的结构通过单晶 X 射线分析得到证实,并通过 DFT 计算支持其形成机制。