Synthesis and reactions of some new 5-carbonyl(4-amino-3-cyano-2-substituted thiophene-5-yl)-8-hydroxyquinoline as possible antimicrobial agents (Part I)

被引：6

作者：

Khalil, ZH

Yanni, AS

Gaber, AM

Abdel-Mohsen, SA

机构：

[1] Univ Hannover, Dept Organ Chem, D-30167 Hannover, Germany

[2] Assiut Univ, Fac Sci, Dept Chem, Assiut 71516, Egypt

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2000年 / 162卷

关键词：

synthesis of some new 5-carbonyl-(substituted thieno[2,3,b]thiophene)-8-hydroxyquinoline; derivatives; antimicrobial activity;

D O I：

10.1080/10426500008045220

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

S-Alkylation of 5-carbonyl-(4-amino-3-cyanothiophene-2-thiol-5-yl)-8-hydroquinoline (4) with several halogen- containing compounds afforded the alkylthio derivatives (5a-f). Treatment of 4 with chloramine gave isothiazolothiophene (7), which was allowed to react with diethylmalonate and/or ethylacetoacetate to give the corresponding pyrimidinoisothiazolothiophenes (8) and (9). Ring closure of 5d-f with ethanolic sodium ethoxide gave thieno[2,3-b]thiophene derivatives (6a-c). Acetic anhydride, ammonium acetate, phenylisothiocyanate, nitrous acid, acetylacetone, phosphorus oxychloride, phosphorus pentachloride, hydrazine hydrate and benzoyl chloride gave further cyclization to construct an additional ring. The structure of the compounds has been established by elemental analysis, IR, NMR and mass spectra. The compounds thus synthesized were screened for their antimicrobial activity.

引用

页码：65 / 80

页数：16

共 16 条

[1] Reactions of α-thiocarboxamidocinnamonitrile derivatives with diethyl malonate:: Synthesis of pyrazolo-[3,4-b]-α-pyridinone, thieno[2,3-b]-α-pyridinone, pyrido[2,3:4′,5′]thieno[2,3-c]pyridazine and pyrido[2,3:4′,5′]thieno[2,3-d]pyrimidinonethione derivatives [J].