Molecules 2007-01-01

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.

Mohammed H Al-Huniti, Mustafa M El-Abadelah, Jalal A Zahra, Salim S Sabri, Arnd Ingendoh

Index: Molecules 12(8) , 1558-68, (2007)

Full Text: HTML

Abstract

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.

Related Compounds

  • 2,4-Dichloro-5-flu...

Related Articles:

Synthesis and antibacterial activity of some novel 4-oxopyrido[2,3-a]phenothiazines.

2014-11-01

[Arch. Pharm. (Weinheim) 347(11) , 861-72, (2014)]

Defluorinated sparfloxacin as a new photoproduct identified by liquid chromatography coupled with UV detection and tandem mass spectrometry.

1998-05-01

[Antimicrob. Agents Chemother. 42(5) , 1151-9, (1998)]

Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid, part VIII [1]. Convenient synthesis and antimicrobial properties of substituted hexahydro[1,4]diazepino[2,3-h]quinoline-9-carboxylic acid and its tetrahydroquino[7,8-b]benzodiazepine analog.

2008-01-01

[Molecules 13(11) , 2880-93, (2008)]

Synthesis and antibacterial properties of new N4-acetylated hexahydro-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acids.

2011-10-01

[J. Enzyme Inhib. Med. Chem. 26(5) , 649-56, (2011)]

Synthesis and antibacterial activity of 9-cyclopropyl-4-fluoro-6-oxo-6, 9-dihydro-[1, 2, 5] thiadiazolo [3, 4-h] quinoline-7-carboxylic acid and its ethyl ester. Al-Qawasmeh RA, et al.

[ARKIVOC 12 , 322-326, (2009)]

More Articles...