A novel, simple and eco-friendly strategy for the synthesis of thiopyrano[4,3-]quinolin-1-ones and pyrrolo[3,4-]quinolin-1-ones from 2-alkynylquinoline-3-carbonitriles and sodium sulphide (NaS·9HO) under catalyst-free conditions at room temperature has been described. In this reaction, a readily available inorganic salt (NaS·9HO) serves as the sulphur source and leads to the generation of diverse functionalized thiopyrano[4,3-]quinolin-1-ones and pyrrolo[3,4-]quinolin-1-ones in moderate to excellent yields through sulfuration, annulation, and aerial oxidation.
View Article and Find Full Text PDFBeilstein J Org Chem
December 2014
The Morita-Baylis-Hillman reaction of acrylamide, as an activated alkene, has seen little development due to its low reactivity. We have developed the reaction using isatin derivatives with acrylamide, DABCO as a promoter and phenol as an additive in acetonitrile. The corresponding aza version with acrylate and acrylonitrile has also been developed resulting in high product yields.
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