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A new type of catalytic cascade pseudo four-component reaction has been found. The simple and facile pseudo four-component reaction of salicylaldehydes and cyclic or heterocyclic ketones with two molecules of malononitrile catalyzed by sodium acetate at ambient temperature results in the formation of 4-substituted 2-amino-4H-chromenes in 70–90% yields. Thus, a new simple and efficient ‘one-pot’ method to synthesize substituted 2-amino-4H-chromenes was found directly from such reasonable starting compounds as salicylaldehydes, cyclic or heterocyclic ketones and malononitrile.

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.

‘One-pot’ AcONa-catalyzed transformation of salicylaldehydes, malononitrile and 4-hydroxy-1-methylquinolin-2(1H)-one in the presence of a minimal quantity of EtOH results in fast (3 min) and efficient formation of unknown 2-amino-4-(2-hydroxyaryl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles in 85–98% yields, which are potential pharmaceutical agents for treating disorders responsive to the induction of apoptosis, antiproliferation, or vascular disruption. This efficient ‘on-solvent’ approach to the 4H-pyrano[3,2-c]quinoline scaffold represents a novel synthetic concept for multicomponent reaction (MCR) strategy and allows to combine the synthetic virtues of conventional MCR with ecological benefits and convenience of facile ‘on-solvent’ procedure.

A new type of catalytic stereoselective cascade pseudo four-component reaction was discovered. The simple and facile pseudo four-component reaction of isatins, cyclic ketones with two molecules of malononitrile catalyzed by triethylamine at ambient temperature stereoselectively results in the formation of tetracyclic spirooxindoles in 60–90% yields. Thus, a new simple and efficient ‘one-pot’ method to synthesize substituted spirooxindoles was found directly from reasonable starting compounds. Unique stereoselectivety was achieved on two or three centers in this pseudo four-component reaction.

‘One-pot’ AcONa-catalyzed transformation of salicylaldehydes, malononitrile and 4-hydroxy-1-methylquinolin-2(1H)-one in the presence of a minimal quantity of EtOH results in fast (3 min) and efficient formation of unknown 2-amino-4-(2-hydroxyaryl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles in 85–98% yields, which are potential pharmaceutical agents for treating disorders responsive to the induction of apoptosis, antiproliferation, or vascular disruption. This efficient ‘on-solvent’ approach to the 4H-pyrano[3,2-c]quinoline scaffold represents a novel synthetic concept for multicomponent reaction (MCR) strategy and allows to combine the synthetic virtues of conventional MCR with ecological benefits and convenience of facile ‘on-solvent’ procedure.

A new type of catalytic stereoselective cascade pseudo four-component reaction was discovered. The simple and facile pseudo four-component reaction of isatins, cyclic ketones with two molecules of malononitrile catalyzed by triethylamine at ambient temperature stereoselectively results in the formation of tetracyclic spirooxindoles in 60–90% yields. Thus, a new simple and efficient ‘one-pot’ method to synthesize substituted spirooxindoles was found directly from reasonable starting compounds. Unique stereoselectivety was achieved on two or three centers in this pseudo four-component reaction.