Murlykina M. Aminoazoles in controlled Doebner-, Groebke- and Ugi-type multicomponent reactions

The study is dedicated to the developing synthetic approaches for the enlargement of molecular diversity of heterocyclic compounds in Doebner-, Groebke- and Ugi-type multicomponent reactions involving aminoazoles by several diversity generation strategies. Selective switching between the alternative directions of Doebner-type reaction involving 5-amino-3-arylpyrazoles or 3-amino-1,2,4-triazole, hydroxy- or methoxy- substituted benzaldehydes and pyruvic acids is possible by means of varying temperature and structure of the starting compounds with obtaining benzoxazocine-, heteroaromatic pyridine- and tetrahydropyrimidinecarboxylic acids; triazolylaminotetrahydro-, 7-hydroxytetrahydro- and dihydropyrimidinecarboxylic acids or pyrrolones. The series of aminoazoles is studied in multicomponent isocyanide reactions. 5-Amino-N-arylpyrazole-4-carboxamide acts as 1,3-binucleophile in Groebke condensation with formation of imidazopyrazolecarboxamides while 3-amino-5-methylisoxazole is the first aminoazole used as an amine component in Ugi reaction with obtaining Ugi products that are further involved in controlled post-transformations depending on the solvent and promoter. Combination of two multicomponent reactions (Doebner- and Ugi-type) allows to introduce azoloazine fragment into the structure of Ugi products as a result of four-component interaction of previously synthesized 6-aryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids, aromatic aldehydes, amines and tert-butylisocyanide. In the current work the molecular diversity of heterocycles is enlarged and 128 new representatives of nitrogen-containing organic compounds with probiotic properties and high activity against A/H1N1 virus are obtained.