Premium
Synthesis of bispiroheterocyclic systems as antimicrobial agents via the reaction of 2‐(cycloalkylidene)‐1‐thia‐4‐azaspiro[4.4]‐nonan‐3‐one and/or [4.5] decan‐3‐one with hydrazines, hydroxylamine, urea and thiourea derivatives
Author(s) -
AlAhmadi Abdullah A.
Publication year - 1996
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/(sici)1097-4660(199602)65:2<200::aid-jctb407>3.0.co;2-u
Subject(s) - chemistry , thiourea , phenylhydrazine , hydrazine (antidepressant) , cyclohexanone , hydrate , hydroxylamine hydrochloride , hydroxylamine , antimicrobial , semicarbazide , medicinal chemistry , pyrimidinones , nuclear chemistry , organic chemistry , chromatography , catalysis
1‐Oxa‐4‐thiaspiro[4.4]nonan‐2‐one ( 1 ) and/or 1‐oxa‐4‐thiaspiro[4.5]‐decan‐2‐one ( 2 ) reacted with 1‐naphthylamine to afford 1‐thia‐4‐(1‐naphthyl)‐4‐azaspiro[4.4]nonan‐3‐one ( 3 ) and/or 1‐thia‐4‐(1‐naphthyl)‐4‐azaspiro[4.5]decan‐3‐one (4). Reactions of 3 and/or 4 with cyclopentanone or cyclohexanone gave the corresponding 2‐cycloalkylidene‐4‐(1‐naphthyl)‐1‐thia‐4‐azaspiro[4.4]nonan‐3‐ones ( 5 and 6 ) and 2‐cycloalkylidene‐4‐(1‐napthyl)‐1‐thia‐4‐azaspiro[4.5]‐decan‐3‐ones ( 7 and 8 ). Reaction of compounds 5 – 8 with hydrazine hydrate, phenylhydrazine, hydroxylamine hydrochloride, urea and thiourea afforded the corresponding bispirothiazolopyrazolines ( 9 – 16 ), bispirothiazoloisoxazolines ( 17 – 20 ), bispirothiazolopyrimidinones ( 21 – 24 ) and bispirothiazolothiopyrimidinones ( 25 – 28 ) respectively. All the synthesized bispiroheterocyclic derivatives were identified by conventional methods (IR, 1 H‐NMR) and elemental analyses. All the prepared compounds were tested for their antimicrobial activities in comparison with tetracycline as a reference compound.