Sodium acetate-catalyzed multicomponent reaction of salicylaldehydes, malononitrile and 3-methyl-2-pyrazolin-5-one initiated by grinding in mortar in the presence of small quantities of water results in the fast (10 min) and efficient formation of substituted 2-amino-4-(1 H -pyrazol-4-yl)-4 H- chromenes in 90–96% yields. The developed fast and efficient approach to the substituted 2-amino-4-(1 H -pyrazol-4-yl)-4 H- chromenes – the promising small-molecule ligands for the treatment of human inflammatory TNFα-mediated diseases and different biomedical applications –, is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast, efficient and environmentally benign synthetic concept for multicomponent reactions strategy.

A new multicomponent reaction (MCR) was found: a sodium acetate-catalyzed transformation of salicylaldehydes, malononitrile and 4-hydroxy-6-methyl-2 H -pyran-2-one in ethanol results in the fast (30 min) and efficient formation of new 4-pyrano-substituted 2-amino-4 H -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-4 H -chromenes in 80–90% yields. This novel ‘one-pot’ process opens an effective and convenient way to pyrano-functionalized 2-amino-4 H -chromene systems, which are promising compounds for different biomedical applications.

The review summarizes and systematizes data on the methods for the preparation of chromeno[2,3-b]pyridines. Both multicomponent and pseudo-multicomponent synthetic approaches and one-pot transformations based on the reactions of carbonyl compounds, malononitrile or its derivatives, and CH-acids are considered. Examples of the use of various catalysts, microwave and ultrasonic radiation, as well as electric current for the implementation of multicomponent transformations of this type are given. Characteristic features of the course and mechanisms of reactions are discussed. Data on the biological activity of the obtained compounds and on other fields of application of such heterocyclic systems are presented. The bibliography includes 109 references.