Firouz Matloubi Moghaddam1, Mohammad Eslami2, Golfamsadat Hoda2. 1. Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Azadi Street, P.O. Box 111559516, Tehran, Iran. matloubi@sharif.edu. 2. Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Azadi Street, P.O. Box 111559516, Tehran, Iran.
Abstract
4H-chromenes play a significant role in natural and pharmacological products. Despite continuous advances in the synthesis methodology of these compounds, there is still a lack of a green and efficient method. In this study, we have designed cysteic acid chemically attached to magnetic graphene oxide (MNPs·GO-CysA) as an efficient and reusable solid acid catalyst to synthesize 4H-chromene skeletons via a one-pot three components reaction of an enolizable compound, malononitrile, an aldehyde or isatin, and a mixture of water-ethanol as a green solvent. This new heterogeneous catalyst provides desired products with a good to excellent yield, short time, and mild condition. This procedure presents an environmentally friendly approach for the synthesis of a great number of 4H-chromene derivatives.
class="Chemical">4H-chromenes play a sigclass="Chemical">nificaclass="Chemical">nt role iclass="Chemical">n class="Chemical">natural aclass="Chemical">nd pharmacological products. Despite coclass="Chemical">nticlass="Chemical">nuous advaclass="Chemical">nces iclass="Chemical">n the syclass="Chemical">nthesis methodology of these compouclass="Chemical">nds, there is still a lack of a greeclass="Chemical">n aclass="Chemical">nd efficieclass="Chemical">nt method. Iclass="Chemical">n this study, we have desigclass="Chemical">ned class="Chemical">n class="Chemical">cysteic acid chemically attached to magnetic graphene oxide (MNPs·GO-CysA) as an efficient and reusable solid acid catalyst to synthesize 4H-chromene skeletons via a one-pot three components reaction of an enolizable compound, malononitrile, an aldehyde or isatin, and a mixture of water-ethanol as a green solvent. This new heterogeneous catalyst provides desired products with a good to excellent yield, short time, and mild condition. This procedure presents an environmentally friendly approach for the synthesis of a great number of 4H-chromene derivatives.
Authors: William Kemnitzer; Shailaja Kasibhatla; Songchun Jiang; Hong Zhang; Jianghong Zhao; Shaojuan Jia; Lifen Xu; Candace Crogan-Grundy; Réal Denis; Nancy Barriault; Louis Vaillancourt; Sylvie Charron; Jennifer Dodd; Giorgio Attardo; Denis Labrecque; Serge Lamothe; Henriette Gourdeau; Ben Tseng; John Drewe; Sui Xiong Cai Journal: Bioorg Med Chem Lett Date: 2005-11-01 Impact factor: 2.823