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 67 条

[11] Dhanabal T, 2006, INDIAN J CHEM B, V45, P523
[12] Antibacterial and antifungal activity of Flindersine isolated from the traditional medicinal plant, Toddalia asiatica (L.) Lam.
Duraipandiyan, V.
Ignacimuthu, S.
[J]. JOURNAL OF ETHNOPHARMACOLOGY, 2009, 123 (03) : 494 - 498
[13] The electrocatalytic cascade assembling of isatins, malononitrile and N-alkyl barbiturates:: An efficient multicomponent approach to the spiro[indole-3,5′-pyrano[2,3-d]pyrimidine] framework
Elinson, Michail N.
Ilovaisky, Alexey I.
Merkulova, Valentina M.
Demchuk, Dmitry V.
Belyakov, Pavel A.
Ogibin, Yuri N.
Nikishin, Gennady I.
[J]. ELECTROCHIMICA ACTA, 2008, 53 (28) : 8346 - 8350
[14] Efficient synthesis of novel spiro[indole-3,6′-pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives through an organobase-catalyzed, three-component reaction
Esmaeili, Abbas Ali
Amini-Ghalandarabad, Saeid
Mesbah, Fariba
Tasmimi, Masoud
Izadyar, Mohammad
Fakhari, Ali Reza
Salimi, Ali Reza
[J]. TETRAHEDRON, 2015, 71 (16) : 2458 - 2462
[15] NON-STEROIDAL ANTIINFLAMMATORY AGENTS .1. SYNTHESIS OF 4-HYDROXY-2-OXO-1,2-DIHYDROQUINOLIN-3-YL ALKANOIC ACIDS BY THE WITTIG REACTION OF QUINISATINES
FABER, K
STUCKLER, H
KAPPE, T
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) : 1177 - 1181
[16] Gilandeh E., 2016, MONATSCCHEM IN PRESS, DOI [10.1007/s00706-016-1788-5, DOI 10.1007/S00706-016-1788-5]
[17] Grieco P.A., 1998, Organic Synthesis in Water
[18] Reaction solvent selection: The potential of water as a solvent for organic transformations
Hailes, Helen C.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) : 114 - 120
[19] The Laccase-Catalyzed Domino Reaction between Catechols and Heterocyclic 1,3-Dicarbonyls and the Unambiguous Structure Elucidation of the Products by NMR Spectroscopy and X-ray Crystal Structure Analysis
Hajdok, Szilvia
Conrad, Ruergen
Leutbecher, Heiko
Strobel, Sabine
Schleid, Thomas
Beifuss, Uwe
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) : 7230 - 7237
[20] Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]-dioxolo [4,5-b]xanthen-9-ones and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones
Heravi, Majid M.
Alinejhad, Hamideh
Bakhtiari, Khadijeh
Oskooie, Hossein A.
[J]. MOLECULAR DIVERSITY, 2010, 14 (04) : 621 - 626

← 1 2 3 4 5 6 7 →