Green and chemoselective synthesis of pyrazolo[3,4-e][1,4]thiazepines and evaluation of their anti-infective activities

被引：0

作者：

Anshu Dandia

Ruby Singh

Jyoti Joshi

Shuchi Maheshwari

机构：

[1] University of Rajasthan,Department of Chemistry

[2] Malaviya National Institute of Technology,Department of Chemistry

来源：

Research on Chemical Intermediates | 2015年 / 41卷

关键词：

Multicomponent reaction; Chemoselectivity; [1,4]Thiazepines; Water; Ultrasound;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

A green and convenient approach to the synthesis of medicinally valuable pyrazolo[3,4-e][1,4]thiazepines via three-component reaction of appropriate aldehydes, 5-amino-3-methylpyrazole, and α-mercaptocarboxylic acids in water under sonication is described. This new protocol provides, via chemoselective synthesis, a new heptacyclic ring system instead of the expected pentacyclic ring system. Experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need of a catalyst are prominent features of this sonocatalyzed procedure. The representative compounds were screened for their in vitro anti-bacterial and anti-tubercular activities.

引用

页码：4213 / 4226

页数：13

共 41 条

[1] Green and chemoselective synthesis of pyrazolo[3,4-e][1,4]thiazepines and evaluation of their anti-infective activities
Dandia, Anshu
Singh, Ruby
Joshi, Jyoti
Maheshwari, Shuchi
RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (07) : 4213 - 4226
[2] Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity
Dandia, Anshu
Singh, Ruby
Joshi, Jyoti
Maheshwari, Shuchi
Soni, Pragya
RSC ADVANCES, 2013, 3 (41): : 18992 - 19001
[3] Nano n-propylsulfonated γ-Al2O3: a new, efficient and reusable catalyst for synthesis of spiro[indoline-3,4-pyrazolo[3,4-e][1,4]thiazepine]diones in aqueous media
Wu, Li Qiang
APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (03) : 148 - 154
[4] Green chemoselective synthesis of thiazolo[3,2-a]pyridine derivatives and evaluation of their antioxidant and cytotoxic activities
Shi, Feng
Li, Chunmei
Xia, Ming
Miao, Kangjie
Zhao, Yanxia
Tu, Shujiang
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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (19) : 5565 - 5568
[5] The synthesis of 5-amino-4-arylazo-3-methyl-1H-pyrazoles and 5-aryl-3-methylpyrazole[3,4-e][1,2,3,4]tetrazines
Yang, Bo
Lu, Yuan
Chen, Chao-Jun
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[6] Three-Component Synthesis of 1,4-[6,6′-(3-Trifluoromethyl-pyrazolo[3,4-d]pyrimidinyl)]piperazines
Fang, Zhengdong
Fang, Di
Chen, Quan
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (02) : 348 - 352
[7] EFFICIENT GREEN APPROACH FOR THE SYNTHESIS OF SPIRO[INDOLINE-3,4′-PYRAZOLO[3,4-b]QUINOLINE] DIONES USING [NMP]H2PO4 AND SOLVATOCHROMIC AND pH STUDIES
Kumari, Sudesh
Sindhu, Jayant
Khurana, J. M.
SYNTHETIC COMMUNICATIONS, 2015, 45 (09) : 1101 - 1113
[8] An efficient and green synthesis of novel highly functionalized nitrogen-fused pyrido[2,3:3,4]pyrazolo[1,5-a]pyrimidine derivatives using recyclable choline hydroxide
Krishnammagari, Suresh Kumar
Jeong, Yeon Tae
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (12) : 7311 - 7329
[9] SILICA SULFURIC ACID AS A SOLID ACID CATALYZED SYNTHESIS OF 4,5,6,7-TETRAHYDRO-2H-PYRAZOLO[3,4-b]PYRIDINE-5-CARBONITRILES AND 1,4-DIARYL-4,5-DIHYDRO-3-METHYL-1H-PYRAZOLO[3,4-b]PYRIDINE-6(7H)-ONES
Mahdavinia, Gholam Hossein
Rahmati, Abbas
REVUE ROUMAINE DE CHIMIE, 2015, 60 (11-12) : 1025 - 1032
[10] An Efficient Synthesis of 1′,7′,8′,9′-Tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]-2,5′(6′H)-dione Derivatives in Aqueous Medium
Zhu, Guangzhou
Gao, Lingli
Yu, Qiuyu
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Xi, Junhua
Rong, Liangce
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (04) : 871 - 878

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