T. Olszewski, B. Boduszek
Nov 6, 2010
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0
Influential Citations
29
Citations
Journal
Tetrahedron
Abstract
abstract An efficient and reliable synthesis of new thiazole-(amino)methylphosphonic, phosphinic acids, andphosphine oxides is reported. The synthetic protocol is based on nucleophilic addition of phosphorousspecies tothiazole derived imines. Unexpectedly, it was discovered that heating of thiazole-2-yl-(amino)-methylphosphonates and phosphinates with aqueous HCl leads to their decomposition resulting ina rupture of the CeP bond, rejecting of the phosphorus containing fragment and formation of the cor-responding secondary N-(thiazole-2-yl-methyl)-alkylamines. Two alternative mechanisms for thiscleavage are postulated. 2010 Elsevier Ltd. All rights reserved. 1. IntroductionSmall and simple heteroaromatics often have surprisinglycomplex biological properties and belong to one of the most im-portant classes of compounds in medicinal chemistry. 1 Especiallyamines containing five-membered heteroaryl groups, such as fu-rans, thiophenes, thiazoles, and pyrazoles are widely found in bothnatural products and drugs.