Multicomponent assembling of salicylaldehydes,malononitrile, and 4-hydroxy-6-methyl-2H-pyran-2-one: A fast and efficient approach to medicinally relevant 2-amino-4H-chromene scaffold |
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Affiliation: | 1. N.D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia;2. A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, 119991 Moscow, Russia |
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Abstract: | A new multicomponent reaction (MCR) was found: a sodium acetate-catalyzed transformation of salicylaldehydes, malononitrile and 4-hydroxy-6-methyl-2H-pyran-2-one in ethanol results in the fast (30 min) and efficient formation of new 4-pyrano-substituted 2-amino-4H-chromenes in 86–96% yields. The same transformation initiated by grinding in mortar in the presence of sodium acetate or potassium fluoride results in a faster (15 min) formation of 4-pyrano-substituted 2-amino-4H-chromenes in 80–90% yields. This novel ‘one-pot’ process opens an effective and convenient way to pyrano-functionalized 2-amino-4H-chromene systems, which are promising compounds for different biomedical applications. |
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Keywords: | MCRs ‘On-solvent’ process Salicylaldehydes Malononitrile |
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