Journal
TETRAHEDRON
Volume 66, Issue 45, Pages 8661-8666Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.09.026
Keywords
Thiazole; Heterocyclic derivatives; Aminophosphonic acids; Cleavage; Amines
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Funding
- Faculty of Chemistry, Wroclaw University of Technology
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An efficient and reliable synthesis of new thiazole-(amino)methylphosphonic, phosphinic acids, and phosphine oxides is reported. The synthetic protocol is based on nucleophilic addition of phosphorous species to thiazole derived imines. Unexpectedly, it was discovered that heating of thiazole-2-yl-(amino)-methylphosphonates and phosphinates with aqueous HCI leads to their decomposition resulting in a rupture of the C-P bond, rejecting of the phosphorus containing fragment and formation of the corresponding secondary N-(thiazole-2-yl-methyl)-alkylamines. Two alternative mechanisms for this cleavage are postulated. (C) 2010 Elsevier Ltd. All rights reserved.
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