Sulfamic Acid Catalyzed Atom Economic, Eco-friendly Synthesis of Novel 7-(Aryl)-10-thioxo-7,9,10,11-tetrahedro-6H-pyrimido-[54:5,6]pyrano[3,2-c]quinoline-6,8(5H)-dione and its Derivatives

被引：6

作者：

Jadhav, Sunetra J. ^{[1
]}

Patil, Reshma B. ^{[1
]}

Kumbhar, Digambar R. ^{[1
]}

Patravale, Ajinkya A. ^{[2
,3
]}

Chandam, Dattatraya R. ^{[2
]}

Deshmukh, Madhukar B. ^{[1
,2
]}

机构：

[1] Shivaji Univ, Dept Agrochem & Pest Management, Kolhapur 416004, Maharashtra, India

[2] Shivaji Univ, Dept Chem, Med Chem Res Lab, Kolhapur 416004, MS, India

[3] Vivekanand Coll, Dept Chem, Kolhapur, MS, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2017年 / 54卷 / 04期

关键词：

ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; NATURAL-PRODUCTS; AQUEOUS-MEDIA; EFFICIENT; PYRANOCOUMARINS; ALKALOIDS; AGENTS; WATER; ANTIBACTERIAL;

D O I：

10.1002/jhet.2807

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel 7-(3-chloro-phenyl)-10-thioxo-7,9,10,11-tetrahedro-6H-pyrimido-[54:5,6] pyrano[3,2-c]quinoline-6,8(5H)-dione derivatives have been synthesized through the multi-component condensation of aromatic aldehydes, barbituric acid, and 2,4-dihydroxy quinoline, using heterogeneous sulfamic acid catalyst in water-ethanol (4:1) solvent system under reflux condition. The present protocol is endowed with charming description such as green synthetic procedure, short reaction time, easy work-up procedure, and excellent yield and high atom economy of pyranoquinoline derivatives. In this study, sulfamic acid is used as a heterogeneous catalyst that is easily recoverable and recyclable. The proposed multi-component reaction has been studied with detail mechanism and spectroscopic data. This is one of the potential greener synthetic approaches to build up the series of pyranoquinoline heterocycles.

引用

页码：2206 / 2215

页数：10

共 13 条

[11] Efficient and facile synthesis of 5-arylindeno[2,1:5,6]pyrido[2,3-d] pyrimidine-2,4(3H)-dione and 7-arylbenzo[h]pyrimido[4,5-b]quinoline-8,10(5H,9H)-dione under mild conditions
Wang, Zhansheng
Wang, Mengyao
Xu, Shuangshuang
Gu, Mengmeng
Meng, Zhiying
Li, Chuan
Cai, Peijun
Rong, Liangce
SYNTHETIC COMMUNICATIONS, 2016, 46 (23) : 1887 - 1892
[12] Facile one-pot green synthesis, antioxidant and antimicrobial activities of 7-(substituted phenyl)-7,11-dihydro-6H,8H-chromeno[3′,4′:5,6]pyrano[2,3-d]pyrimidine-6,8,10(9H)-trione derivatives
Vanukuri, Omkar Reddy
Gundluru, Mohan
Bellala, Poojitha
Dachuru, Rama Sekhara Reddy
Cirandur, Suresh Reddy
SYNTHETIC COMMUNICATIONS, 2025,
[13] BASE-CATALYZED CYCLOADDITION ON 3-CARBETHOXY-6-CHLOROCOUMARIN - SYNTHESIS OF 10-SUBSTITUTED 2-CHLORO-6A, 7,8,9,10,10A-HEXAHYDRO-6H-DIBENZO[B,D]PYRAN-6,7,9-TRIONES, 1-SUBSTITUTED 9-CHLORO-1,2,3,4,4A,10A-HEXAHYDRO-5H-[1]BENZOPYRANO[3,4-C]PYRIDINE-2,4,5-TRIONES AND 2-CHLORO-6A,7,8,9,10,11,12,12A-OCTAHYDRO-6H-[1]BENZOPYRANO[3,4-C]QUINOLINE-6,7-DIONED
HASSAN, MA
ELBORAI, M
ELWY, AM
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1981, 20 (09): : 815 - 816

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