ONE-FLASK SYNTHESES OF SOME NEW SPIROTHIAZOLOPYRANOPYRAZOLE, SPIROTHIAZOLODIHYDROPYRIDINOPYRAZOLE AND SPIROTHIAZOLOTHIOPYRANOPYRAZOLE DERIVATIVES AS ANTIMICROBIAL AGENTS
Aa. Alahmadi, ONE-FLASK SYNTHESES OF SOME NEW SPIROTHIAZOLOPYRANOPYRAZOLE, SPIROTHIAZOLODIHYDROPYRIDINOPYRAZOLE AND SPIROTHIAZOLOTHIOPYRANOPYRAZOLE DERIVATIVES AS ANTIMICROBIAL AGENTS, Phosphorus, sulfur and silicon and the related elements, 122, 1997, pp. 121-132
1-Thia-4-benzyl-4-azaspiro[4.4]nonan-3-one (2a) and/or 1-thia-4-benzyl
-4-azaspiro [4.5]decan-3-one (2b) reacted with 4-arylidene-3-methylpyr
azolin-5-ones (1a-f) in a mixture of ethanol/pyridine at reflux temper
ature to give spirothiazolopyranopyrazoles (3a-1) in one flask. The fu
sion of compounds 1a-f with 2a and/or 2b in the presence of ammonium a
cetate afforded spirothiazolodihydropyridinopyrazole derivatives (4a-1
) in good yields. Also the reaction of compounds 1a-f with 2a and/or 2
b with phosphorus pentasulfide in pyridine at reflux temperature yield
ed the spirothiazolothiopyranopyrazoles (5a-1). All the synthesized sp
iroheterocyclic derivatives were identified by conventional methods (I
R, H-1-NMR) and elemental analyses. All the prepared compounds were te
sted for their antimicrobial activities in comparison with tetracyclin
e as a reference compound.