Chemistry of substituted quinolines:: Thieno[2,3-b] and thiopyrano[2,3-b]quinolines

被引：16

作者：

Kiran, Balaji M. ^{[1
]}

Nandeshwarappa, Belalakatte P. ^{[1
]}

Vaidya, Vijayavittala P. ^{[1
]}

Mahadevan, Kittappa M. ^{[1
]}

机构：

[1] Kuvempu Univ, Dept Postgrad Studies & Res Chem, Shankaraghatta 577451, Karnataka, India

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2007年 / 182卷 / 05期

关键词：

3-formyl-2-chloroquinolines; 3-formyl-2-mercaptoquinolines; 3-formyl(quinolin-2-yl)thio acetic acids; methyl thieno[2,3-b]quinoline-2-carboxylates; thieno[2,3-b]quinolines; thiopyrano[2,3-b]quinolines;

D O I：

10.1080/10426500601088846

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.

引用

页码：969 / 980

页数：12