One pot synthesis using supported reagents system KSCN/SiO2-RNH3OAc/Al2O3: synthesis of 2-aminothiazoles and N-allylthioureas

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles and N-allylthioureas from commercially available materials in one pot by using a supported reagents system, KSCN/SiO2-RNH3OAc/Al2O3, in which alpha-halo ketone reacts first KSCN/SiO2 and the product, alpha.-thiocy...

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Bibliographic Details
Published inTetrahedron Vol. 62; no. 14; pp. 3201 - 3213
Main Authors Aoyama, T, Murata, S, Arai, Araki, N, Takido, T, Suzuki, Y, Kodomari, M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 03.04.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
ISOTHIOCYANATES
KETONES
ALKYL THIOCYANATES
thiazoles
POTASSIUM THIOCYANATE
REGIOSELECTIVE SYNTHESIS
thioureas
one pot process
INHIBITORS
DERIVATIVES
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Summary:A simple and efficient method has been developed for the synthesis of 2-aminothiazoles and N-allylthioureas from commercially available materials in one pot by using a supported reagents system, KSCN/SiO2-RNH3OAc/Al2O3, in which alpha-halo ketone reacts first KSCN/SiO2 and the product, alpha.-thiocyanatoketone, reacts with RNH3OAc/Al2O3 to give the final product, 2-aminothiazoles, in good yield and allyl bromide reacts with KSCN/SiO2 and the product, allyl isothiocyanate, reacts with RNH3OAc/Al2O3 to give N-allylthiourea. (c) 2006 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2006.01.075