title: A new multicomponent reaction: unexpected formation of derivatizable cyclic α-alkoxy isothioureas.
abstract: An unexpected formation of cyclic α-alkoxy isothioureas has been achieved. As is known, the heterocyclic imines 2,5-dihydro-1,3-thiazoles are convertible to bisamides with the aid of a carboxylic acid and an isocyanide (Ugi reaction). Herein, it is shown that 2,5-dihydro-1,3-thiazole S-monoxides-the respective α-sulfinyl imines-are characterized by an altered reaction behavior. In a hitherto unknown multicomponent reaction the α-sulfinyl imines react with an isocyanide under acidic conditions in an alcoholic solution to the respective α-alkoxy isothioureas in good yields. In addition to the investigations on this unexpected synthesis the regioselectivity of the acylation of the synthesized compounds is described. A rearrangement, which is accelerated by EDC and HOBt, between both possible regioisomers was found.
authors: Institut für Chemie, Carl von Ossietzky Universität Oldenburg, P. O. Box 2503, Carl-von-Ossietzky-Str. 9-11, 26111 Oldenburg, Germany. juergen.martens@uni-oldenburg.de.
authors: Fabian
authors: F
authors: Brockmeyer
authors: Valentin
authors: V
authors: Morosow
authors: Jürgen
authors: J
authors: Martens
mesh_terms: D003486:Cyanides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013844:Thiazoles / Q000737:chemistry*; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003486:Cyanides; D007097:Imines; D013844:Thiazoles; D013890:Thiourea