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Synthesis 2006(1): 133-145
DOI: 10.1055/s-2005-918490
DOI: 10.1055/s-2005-918490
PAPER
© Georg Thieme Verlag Stuttgart · New YorkTitanium(IV) Chloride Promoted Syntheses of New Imidazo[1,2-a]pyridine Derivatives under Microwave Conditions
Weitere Informationen
Received
6 May 2005
Publikationsdatum:
24. November 2005 (online)
Publikationsverlauf
Publikationsdatum:
24. November 2005 (online)
Abstract
A new method is described for the synthesis of imidazo[1,2-a]pyridine derivatives from the reaction of 2-aminopyridines with α-haloketones. The critical reagent is titanium(IV) chloride, which appears to serve as a strong dehydrating agent to promote formation of putative Schiff base intermediates, which cyclize subsequently to form the products. The reactions were performed rapidly under microwave conditions. Multiple reaction conditions were evaluated, including reaction temperature, solvent and other Lewis acids. Various combinations of substitution patterns in both the α-haloketone and 2-aminopyridine substrates were examined to evaluate the scope of the reaction. The reaction is quite sensitive to substituents in both substrates, especially those with basicity or coordination ability.
Keywords
titanium(IV) chloride - imidazo[1,2-a]pyridine - polycyclic - condensation - Schiff base formation - microwave
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