(Propargylsulfanyl)-2-aza-1,3,5-trienes as a direct source for novel family of highly functionalized 4,5-dihydro-1,3-thiazoles

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• 作者：Nina A. Nedolya ; ^{nina@irioch.irk.ru} ; Ol'ga A. Tarasova ; Alexander I. Albanov ; Lyudmila V. Klyba ; Boris A. Trofimov ; ^{boris_trofimov@irioch.irk.ru}
• 关键词：5-Ethenylidene-4 ; 5-dihydro-1 ; 3-thiazoles ; (Propargylsulfanyl)-2-aza-1 ; 3 ; 5-trienes ; Alkoxyallenes ; Isothiocyanates ; Propargyl bromide
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：23 February 2017
• 年：2017
• 卷：73
• 期：8
• 页码：1085-1097
• 全文大小：2439 K
• 卷排序：73

文摘

A novel, simple approach to 2-(1-alkoxyprop-1-enyl)-5-ethenylidene-4,5-dihydro-1,3-thiazoles has been disclosed through the reaction of (propargylsulfanyl)-2-aza-1,3,5-trienes (readily available from alkoxyallenes, isothiocyanates, and propargyl bromide) with potassium or sodium tert-butoxide (1.1–1.4 equiv) under mild conditions [DMSO/THF (∼1:4–5), ca. −30 °C, 15–30 min]. The process proceeds through deprotonation of an activated SCH2 group, followed by intramolecular [1,5]-ring-closure. Unlike alkyl-, benzyl-, and allylsulfanyl-analogues, the exclusive or competitive formation of seven-membered azaheterocycles was not observed.