ONE POT SYNTHESIS OF IMIDAZOLE-TRIAZOLE FRAMEWORK VIA DIMORTH REARRANGEMENT AND CLICK REACTION.
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Author(s):
P.CHANTI BABU, R.S.K.SHARMA, B.JAYARAM
Vol - 4, Issue- 2 ,
Page(s) : 742 - 756
(2013 )
DOI : https://doi.org/10.32804/IRJMSH
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Abstract
There are only a few approaches that describe the direct synthesis of 2- aminoimidazoles and their biological activity1-5. The earliest method involves condensation of α-aminocarbonyl compounds with cyanamide or their synthetic equivalents6, 7. This method is most commonly used for the direct construction of the 2-aminoimidazole ring. Other general applicable strategies are cyclocondensation of α-bromoketone with N-acetylguanidine in acetonitrile8, iminophosphorane-mediated cyclization of α –azido esters9, ammonolysis of 2-amino-1,3-oxazol-3-iumsalts10, sequential functionalization of 1,2-diprotected imidazole ring with different electrophiles11. Most of them involve long experimental procedures, the use of unstable precursors and tiresome workup process. Accordingly, the development of straightforward and general procedures for the synthesis of diversely substituted 2- aminoimidazoles from readily available precursors is highly warranted. Herein, we report a rapid and highly efficient Cu-mediated synthesis of 2-aminoimidazoletriazole framework via click reaction and dimorth rearrangement.
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