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Molecules 2007, 12(8), 1558-1568; doi:10.3390/12081558
Article

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

1
,
1, 1,* , 2
 and
3
1 Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan 2 University of Sharjah, Sharjah, P. O. Box 27272, United Arab Emirates (UAE) 3 Bruker Daltonik GmbH, Fahrenheitstr. 4, D-28359 Bremen, Germany
* Author to whom correspondence should be addressed.
Received: 4 June 2007 / Revised: 19 July 2007 / Accepted: 19 July 2007 / Published: 27 July 2007
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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 raction 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.
Keywords: 7-Chloro -8-nitro-4-oxoquinoline-3-carboxylic acid; 3-mercaptopropanoic 7-Chloro -8-nitro-4-oxoquinoline-3-carboxylic acid; 3-mercaptopropanoic
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Al-Huniti, M.H.; El-Abadelah, M.M.; Zahra, J.A.; Sabri, S.S.; Ingendoh, A. 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. Molecules 2007, 12, 1558-1568.

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