Convenient preparation of 4-arylmethyl- and 4-hetarylmethyl thiazoles by regioselective cycloaddition reactions of 3-sulfanyl- and selanylpropargyl alcohols

Autor:	Teruhisa Yamamoto, M. Matsui, Mitsuhiro Yoshimatsu, Arisa Sawa
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Organic Chemistry Regioselectivity Propargyl alcohol Biochemistry Chemical synthesis Cycloaddition chemistry.chemical_compound chemistry Sulfanyl Drug Discovery Propargyl Organic chemistry Thiazole Thioamide
Zdroj:	Tetrahedron. 66:7975-7987
ISSN:	0040-4020
DOI:	10.1016/j.tet.2010.08.015
Popis:	Complete details of thiazole syntheses by scandium-catalyzed cycloaddition reactions of 1-aryl- and 1,1-bisaryl-3-phenylsulfanylpropargyl alcohols with thioamides are described. Reactions of 1,1-bisarylpropargyl alcohols with thioamides and selenamide in MeNO 2 /H 2 O resulted in 4-bisarylmethyl-1,3-thiazoles 4aa – ic and 4H-4,4-bisaryl-1,3-thiazines 5ea – ga in high yields. Reactions in MeNO 2 /D 2 O resulted in 4-bisaryldeuteriomethyl-1,3-thiazoles 10ca – ia with high deuterium purity. Reactions of dialkyl and alkyl aryl propargyl alcohols are also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b83d7836b4251cb084becf8676360cc6 https://doi.org/10.1016/j.tet.2010.08.015 Zobrazit plný text záznamu Full Text from ScienceDirect