1600501-17-4Relevant academic research and scientific papers
(Propargylsulfanyl)-2-aza-1,3,5-trienes as a direct source for novel family of highly functionalized 4,5-dihydro-1,3-thiazoles
Nedolya, Nina A.,Tarasova, Ol'ga A.,Albanov, Alexander I.,Klyba, Lyudmila V.,Trofimov, Boris A.
, p. 1085 - 1097 (2017)
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 SCH2group, 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.
Structural reorganization of (allyl-, benzyl-, and propargylsulfanyl)- substituted 2-aza-1,3,5-trienes in t-BuOK/THF/DMSO: Access to rare functionalized 2-thiazolines
Nedolya, Nina A.,Tarasova, Ol'Ga A.,Albanov, Alexander I.,Trofimov, Boris A.
, p. 2495 - 2498 (2014/05/06)
Treatment of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes, which are readily accessible from lithiated methoxyallene, isopropyl isothiocyanate, and allyl, benzyl, or propargyl bromide, respectively, with t-BuOK in THF/DMSO resu
