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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
Received: 4 June 2007; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Al-Huniti MH, El-Abadelah MM, Zahra JA, Sabri SS, 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(8):1558-1568.

Chicago/Turabian Style

Al-Huniti, Mohammed H.; El-Abadelah, Mustafa M.; Zahra, Jalal A.; Sabri, Salim S.; Ingendoh, Arnd. 2007. "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 12, no. 8: 1558-1568.


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