Heterocycles [h]fused onto 4-oxoquinoline-3-carboxylic acid, part IV. Convenient synthesis of substituted hexahydro [1,4]thiazepino[2,3-h]quinoline-9-carboxylic acid and its tetrahydroquino[7,8-b]benzothiazepine homolog.
Substituted [1,4]thiazepino[2,3-h]quinolinecarboxylic acid 3 is prepared by PPA-catalyzed thermal lactamization of the respective 8-amino-7-[(2-carboxyethyl)thio]-1,4-dihydroquinoline-3-carboxylic acid 9. The latter synthon is obtained by reduction of the 8-nitro-1,4-dihydroquinoline precursor 8 which, in turn, is made accessible via interaction of 3-mercaptopropionic acid with 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydroquinoline-3-carboxylic acid 7 in the presence of triethylamine. A benzo-homolog of 3, namely tetrahydroquino[7,8-b]benzothiazepine-3-carboxylic acid 6, is analogously prepared via the reaction of 2-mercaptobenzoic acid with 7, followed by reduction of the resulting 7-[(2-carboxyphenyl)thio]-8-nitro product 10 into the corresponding 8-amino derivative 11, and subsequent lactamization. The structures assigned to 3, 6 and 8-11 are based on microanalytical and spectral (IR, MS, NMR) data.
Al-Huniti
Mohammed H
MH
Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan. m.alhuniti@ju.edu.jo
El-Abadelah
Mustafa M
MM
Zahra
Jalal A
JA
Sabri
Salim S
SS
Ingendoh
Arnd
A
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry*; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry
C524598:2,8-dioxohexahydro(1,4)thiazepino(2,3-h)quinoline; D000890:Anti-Infective Agents; D011804:Quinolines; D015363:Quinolones; D013841:Thiazepines; C524599:tetrahydroquino(7,8-b)(1,4)benzothiazepine