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
  • [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] PYRAZOLO[3,4-E][1,4]THIAZEPINES - SYNTHESIS AND STRUCTURE PROOF
    SWETT, LR
    RATAJCZYK, JD
    NORDEEN, CW
    AYNILIAN, GH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (06) : 1137 - 1142
  • [3] 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
  • [4] POSSIBLE PSYCHOPHARMACOLOGICAL AGENTS .3. SYNTHESIS AND CNS ACTIVITY OF SOME NEW FLUORINE-CONTAINING PYRAZOLO[3,4-E][1,4]THIAZEPINES
    JOSHI, KC
    DUBEY, K
    PHARMAZIE, 1979, 34 (11): : 716 - 718
  • [5] SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF SOME PYRAZOLO[3,4-E][1,4]-DIAZEPIN-4,7-DIONES
    MIGLIARA, O
    FLUGY, A
    NOVARA, V
    GAGLIANO, M
    FARMACO, 1992, 47 (01): : 111 - 119
  • [6] Routes to pyrazolo[3,4-e][1,4]thiazepine, pyrazolo[1,5-a]pyrimidine and pyrazole derivatives
    Abu Elmaati, TM
    El-Taweel, FMA
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2003, 50 (3A) : 413 - 418
  • [7] SYNTHESIS OF A PYRAZOLO[3,4-E]-1,4,2-DITHIAZINE DERIVATIVE
    DEANE, CC
    JOURNAL OF CHEMICAL RESEARCH-S, 1986, (10): : 388 - 389
  • [8] SYNTHESIS OF 1,3,4-TRIPHENYL-1H-PYRAZOLO[3,4-E][1,4]THIAZEPINE-7-ONE
    VARTANYAN, RS
    GYULBUDAGYAN, AL
    VARTANYAN, SA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1984, (04): : 464 - 465
  • [9] POTENTIAL ANTITUMOR AGENTS .3. SYNTHESIS OF PYRAZOLO[3,4-E]PYRROLO[3,4-G]INDOLIZINE AND 1H-PYRAZOLO[3,4-E]INDOLIZINE DERIVATIVES
    ARTICO, M
    MASSA, S
    STEFANCICH, G
    SILVESTRI, R
    DISANTO, R
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (02) : 503 - 507
  • [10] Green synthesis and anti-infective activities of fluorinated pyrazoline derivatives
    Shelke, Sharad N.
    Mhaske, Ganesh R.
    Bonifacio, Vasco D. B.
    Gawande, Manoj B.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (17) : 5727 - 5730