Heterocycles hFused onto 4-Oxoquinoline-3-Carboxylic Acid, Part IV. Convenient Synthesis of Substituted Hexahydro 1,4Thiazepino2,3-hquinoline-9-carboxylic Acid and Its Tetrahydroquino7,8-bbenzothiazepine HomologReportar como inadecuado


Heterocycles hFused onto 4-Oxoquinoline-3-Carboxylic Acid, Part IV. Convenient Synthesis of Substituted Hexahydro 1,4Thiazepino2,3-hquinoline-9-carboxylic Acid and Its Tetrahydroquino7,8-bbenzothiazepine Homolog


Heterocycles hFused onto 4-Oxoquinoline-3-Carboxylic Acid, Part IV. Convenient Synthesis of Substituted Hexahydro 1,4Thiazepino2,3-hquinoline-9-carboxylic Acid and Its Tetrahydroquino7,8-bbenzothiazepine Homolog - Descarga este documento en PDF. Documentación en PDF para descargar gratis. Disponible también para leer online.

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.



Abstract Substituted 1,4thiazepino2,3-hquinolinecarboxylic acid 3 is prepared by PPA-catalyzed thermal lactamization of the respective 8-amino-7-2-carboxyethylthio- 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 tetrahydroquino7,8-bbenzothiazepine-3-carboxylic acid 6, is analogously prepared via the raction of 2-mercaptobenzoic acid with 7, followed by reduction of the resulting 7-2-carboxyphenylthio-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. View Full-Text

Keywords: 7-Chloro -8-nitro-4-oxoquinoline-3-carboxylic acid; 3-mercaptopropanoic 7-Chloro -8-nitro-4-oxoquinoline-3-carboxylic acid; 3-mercaptopropanoic





Autor: Mohammed H. Al-Huniti 1, Mustafa M. El-Abadelah 1, Jalal A. Zahra 1,* , Salim S. Sabri 2 and Arnd Ingendoh 3

Fuente: http://mdpi.com/



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