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DETAILS OF A MULTICOMPONENT BIGINELLI REACTION INVOLVING 3-OXOBUTANOYL-CONTAINING PODANDS, AROMATIC ALDEHYDES, AND 1,2,4-TRIAZOLE-3-AMINE

Елена С. Филатова, Ольга В. Федорова, Константин А. Чистяков, Геннадий Л. Русинов, Валерий Н. Чарушин
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Abstract


A reaction of 3-oxobutanoyl-containing podands with thiophene-2-carbaldehyde (or benzaldehyde) and 3-amino-1,2,4-triazole gave podands featuring a 4,7-dihydro[1,2,4]triazolo[1,5-а]pyrimidine motif. It was established that the process was accompanied by the formation of [4,3-а]-isomers, which occurred in a slight excess during the synthesis of a podand containing a phenyl group at position 7 and, on the other hand, were observed as the minor products during the synthesis of podands bearing a thiophen-2-yl substituent. Trace amounts of monosubstituted podands were also detected, containing a free hydroxy group along with the triazolodihydropyrimidine pharmacophore.

Keywords


dihydropyrimidine; triazolo[1,5-а]pyrimidine; triazolo[4,3-а]pyrimidine; monosubstituted podand; podand; tuberculostatic activity

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