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Diversity-oriented Cascade Synthesis of Pyrido[2\',3\':4,5]thieno[2,3-b]pyridine Derivatives
Published: 31 October 2011 by MDPI in The 15th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: A library of 2-amino-9-aryl-3-cyano-4-methyl-7-oxo-6,7,8,9-tetrahydropyrido[2\',3\':4,5]thieno[2,3-b]pyridines which recently have been reported as selective progesterone receptor agonists was synthesized by ternary condensation of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with malononitrile and acetone, and alternatively by reaction of bis(4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-yl)disulfides with acetone and malononitrile in basic media. The mechanism, scope and limitations of the reactions are discussed.
Keywords: dipyridothiophenes, thienopyridines, progesterone receptor agonists, cascade heterocyclization