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An expeditious synthesis of imidazo[1,2-a]pyridines through nucleophile induced ring transformation reactions of 6-aryl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitriles

✍ Scribed by Vishnu Ji Ram; Nidhi Agarwal; Ashoke Sharon; Prakas R Maulik


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
107 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


An efficient and convenient synthesis of 2-(5-aryl-8-nitro-2,3-dihydroimidazo[1,2-a]pyridin-7(1H)-ylidene)acetonitriles (3) and 6-aryl-4-{2-[(E)-nitromethylidene]-1-imidazolidinyl}-2-oxo-2H-pyran-3-carbonitriles (4) through nucleophile induced ring transformation of suitably functionalized 2H-pyran-2-one (1) from imidazoliden-2-ylidene nitromethane is delineated.


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Suitably functionalized 3-carbomethoxy/cyano-2H-pyran-2-ones are excellent synthons for the synthesis of arenes and heteroarenes of therapeutic importance. The compounds 6-aryl-3-cyano-4-methylsulfanyl-2H-pyran-2-ones have been transformed into bridgedhead azolopyrimidines and imidazothiazines throu