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
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
收藏
页码:4213 / 4226
页数:13
相关论文
共 50 条
  • [21] Efficient one-pot synthesis of spiro[indoline-3,4′-pyrazolo[3,4-e][1,4]thiazepine]dione via three-component reaction
    Chen, Hui
    Shi, Daqing
    TETRAHEDRON, 2011, 67 (31) : 5686 - 5692
  • [22] Efficient catalyst-free tricomponent synthesis of new spiro[cyclohexane-1,4′-pyrazolo[3,4-e][1,4]thiazepin]-7′(6′H)-ones
    Becerra-Rivas, Christian
    Cuervo-Prado, Paola
    Orozco-Lopez, Fabian
    SYNTHETIC COMMUNICATIONS, 2019, 49 (03) : 367 - 376
  • [23] SYNTHESIS OF 1H-PYRAZOLO[3,4-E]-S-TRIAZOLO[3,4-C]-AS-TRIAZINES, 8H-PYRAZOLO[3,4-E]TETRAZOLO[5,1-C]AS-TRIAZINE AND 1,7-DIHYDRO-8H-PYRAZOLO[3,4-E]-AS-TRIAZINE DERIVATIVES
    YOUSSEF, MSK
    HASSAN, KM
    ATTA, FM
    ABBADY, MS
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (05) : 1565 - 1568
  • [24] Synthesis and structural analysis of 1,4′-pyrazolo[3,4-e][1,4]thiazepin-7′ (6H)ones: An example of conformational chirality in seven-membered heterocycles
    Orozco-Lopez, Fabian
    Cobo, Justo
    Becerra, Christian A.
    Cuervo-Prado, Paola A.
    Macias, Mario A.
    JOURNAL OF MOLECULAR STRUCTURE, 2025, 1322
  • [25] Synthesis of new Di-, Tetra-, and hexahydropyrazolo[3,4-e][1,4]diazepine derivatives
    A. V. Bol’but
    S. V. Kemskii
    M. V. Vovk
    Russian Journal of Organic Chemistry, 2012, 48 : 991 - 1002
  • [26] Synthesis of new Di-, Tetra-, and hexahydropyrazolo[3,4-e][1,4]diazepine derivatives
    Bol'but, A. V.
    Kemskii, S. V.
    Vovk, M. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (07) : 991 - 1002
  • [27] Pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones .1. Synthesis and in vitro antimicrobial evaluation
    Bruni, F
    Selleri, S
    Costanzo, A
    Guerrini, G
    Casilli, NL
    Sacco, C
    Donato, R
    FARMACO, 1996, 51 (06): : 451 - 455
  • [28] A NEW ROUTE TO PYRAZOLO[3,4-E]-1,2,4-TRIAZINES
    SADEK, KU
    ABOUHADID, K
    ELGHANDOUR, AHH
    LIEBIGS ANNALEN DER CHEMIE, 1989, (05): : 501 - 502
  • [29] Sonochemical synthesis of novel pyrano[3,4-e][1,3]oxazines: A green protocol
    Saleh, Tamer S.
    Al-Bogami, Abdullah S.
    Mekky, Ahmed E. M.
    Alkhathlan, Hamad Z.
    ULTRASONICS SONOCHEMISTRY, 2017, 36 : 474 - 480
  • [30] A green and efficient synthesis of furo[3,4-e]pyrazolo[3,4-b]pyridine derivatives in water under microwave irradiation without catalyst
    Shi, Feng
    Wang, Qian
    Tu, Shujiang
    Zhou, Jianfeng
    Jiang, Bo
    Li, Chunmei
    Zhou, Dianxiang
    Shao, Qingqing
    Cao, Longji
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (04) : 1103 - 1108