Heterocycles [h]-Fused onto 4-Oxoquinoline-3-carboxylic Acid. Part X [1]. Synthesis and X-Ray Structure of a Model 4- Oxo[1,4]benzoxazepino[2,3-h]quinoline-3-carboxylic Ester-Reference-Cited by-同舟云学术

Heterocycles [h]-Fused onto 4-Oxoquinoline-3-carboxylic Acid. Part X [1]. Synthesis and X-Ray Structure of a Model 4- Oxo[1,4]benzoxazepino[2,3-h]quinoline-3-carboxylic Ester

Published:2013-02-01 Issue:2 Volume:68 Page:187-194
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:en
Short-container-title:

Author:

Farrayeh Batool A.¹,El-Abadelah Mustafa M.¹,Zahra Jalal A.¹,Haddad Salim F.¹,Voelte Wolfgang²

Affiliation:

1. Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan

2. Interfakultäres Institut für Biochemie, Universität Tübingen, Hoppe-Seyler-Straße 4, 72076 Tübingen, Germany

Abstract

Direct interaction of salicylaldehyde oxyanion with ethyl 7-chloro-8-nitro-4-oxoquinoline-3- carboxylate (2) delivered the respective 7-(2-formyl-phenoxy)-8-nitro-4-oxoquinoline-3-carboxylic ester 3. Reductive cyclization of 3 furnished the corresponding 4-oxo-[1,4]benzoxazepino[2,3- h]quinoline-3-carboxylic ester 5. Acid-catalyzed hydrolysis of the esters 3/5 produced the respective acids 4/6. Structural assignments for the new compounds 3 - 6 are supported by microanalytical and spectral (IR, HRMS, NMR) data and confirmed by X-ray structure determination for compound 5. Interestingly, compound 6 exhibited good antifungal activity against C. albicans.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.5560/znb.2013-2270/pdf

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