Single-Pot Preparation of 4-Amino-2-(het)aryl-5-Substituted Thiazoles Employing Functionalized Dithioesters as Thiocarbonyl Precursors
Anusha Avadhani, P. Iniyavan, Yogendra Kumar, Hiriyakkanavar Ila
Abstract
An effective, diversity oriented, one-pot reaction of 4-amino-2-(het)aryl/alkyl-5-functionalized thiazoles has been disclosed, utilizing aryl/heteroaryl/alkyl dithioesters as thiocarbonyl coupling partners in a modified Thorpe-Ziegler type cyclization. The reaction proceeds at room temperature, under mild conditions, in excellent yields, displaying broad functional group compatibility at 2 and 5 positions of thiazoles. This synthetic strategy has been further expanded for the one-pot construction of two highly potent tubulin polymerization inhibitors, i.e., 2-(het)aryl-4-amino-5-(3,4,5-trimethoxyaroyl) thiazoles, in high yields.
Topics & Concepts
ChemistryArylAlkylPolymerizationOne-pot synthesisCombinatorial chemistryReaction conditionsOrganic chemistryPolymer chemistryPolymerCatalysisSynthesis of heterocyclic compoundsSynthesis and biological activityFerrocene Chemistry and Applications