Shin, Dongyun Lee, Jihoon Hahn, Hoh-Gyu 2024-01-20T19:01:03Z 2024-01-20T19:01:03Z 2021-09-04 2010-07-24 0040-4020 https://pubs.kist.re.kr/handle/201004/131242 2-Iminothiazole, an isoform of 2-aminothiazole, is a scaffold of synthetic and medicinal significance. We have reported an efficient method by which alkyl group of 2-alkyliminothiazoles is changed into other alkyl groups by isothiocyanates. In this article, a detailed mechanistic aspect, and the scopes and limitations were disclosed. All the reactions were carried out in toluene at 105 degrees C without any additive. The reaction is a reversible process and the equilibrium is determined by the reactivity of both reactants, in which the more electron-withdrawing alkyl or aryl groups at the 2-imino group or isothiocyanate showed higher reactivities. With this simple method, we effectively altered the alkyl group attached on the imine nitrogen. A synthetic problem in 2-iminothiazole chemistry, synthesis of amino acid-derived 2-iminothiazole was solved in a very simple manner. Using suitably designed 2-iminothiazole substrate, the electrophilic reactivity of various isothiocyanates could be empirically compared by this exchange reaction. Moreover, successful exchange reaction using isocyanates instead of isothiocyanates broadened the utility of this reaction. (C) 2010 Published by Elsevier Ltd. English PERGAMON-ELSEVIER SCIENCE LTD REGIOSELECTIVITY INHIBITORS DISCOVERY CHEMISTRY PYRROLES Intermolecular alkyl/aryl exchange of 2-iminothiazoles with isothiocyanates and isocyanates: scopes and limitations Article 10.1016/j.tet.2010.05.015 1 TETRAHEDRON, v.66, no.30, pp.5707 - 5713 TETRAHEDRON 66 30 5707 5713 scie scopus 000279988000022 2-s2.0-77955922058 Chemistry, Organic Chemistry Article REGIOSELECTIVITY INHIBITORS DISCOVERY CHEMISTRY PYRROLES Synthesis Medicinal Iminothiazole Thiazole Isothiocyanate Isocyanate