In(OTf)3 catalysed an expeditious synthesis of β-carboline-imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazine conjugates

被引：31

作者：

Devi, Nisha ^{[1
]}

Singh, Dharmender ^{[1
]}

Honey ^{[1
]}

Mor, Satbir ^{[2
]}

Chaudhary, Sandeep ^{[3
]}

Rawal, Ravindra K. ^{[4
]}

Kumar, Vipin ^{[1
]}

Chowdhury, Asim K. ^{[1
]}

Singh, Virender ^{[1
]}

机构：

[1] Dr BR Ambedkar Natl Inst Technol NIT Jalandhar, Dept Chem, Jalandhar 144011, Punjab, India

[2] GJ Univ Sci & Technol Hisar, Dept Chem, Hisar 125001, Haryana, India

[3] Malaviya Natl Inst Technol Jaipur MNIT, Dept Chem, Jaipur 302017, Rajasthan, India

[4] Indosoviet Friendship Coll Pharm, Dept Pharmaceut Chem, Moga 142001, Punjab, India

来源：

RSC ADVANCES | 2016年 / 6卷 / 50期

关键词：

NONREARRANGED MONOTERPENOID UNIT; SIMPLE INDOLE ALKALOIDS; BETA-CARBOLINE DERIVATIVES; EUKARYOTIC TOPOISOMERASE-II; BLACKBURN-BIENAYME REACTION; SOLVENT-FREE CONDITIONS; BIOLOGICAL EVALUATION; ANTITUMOR AGENTS; INDIUM TRIFLATE; ANTICANCER ACTIVITY;

D O I：

10.1039/c6ra04841b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

beta-Carboline containing alkaloids are ubiquitously present in Nature, while imidazo[1,2-a]pyridine nucleus is incorporated in various synthetic commercial drugs and biologically previliged moieties. On this basis, new beta-carboline-imidazoazine conjugates were designed and a small library of compounds integrating both the pharmacophores was constructed with 4-points of diversity by using the In(OTf)(3) assisted Groebke-Blackburn-Bienayme multicomponent strategy. The methodology was found to be simple and convenient for the efficient syntheses of beta-carboline-imidazo[1,2-a]azine conjugates. The present synthetic protocol provides several advantages like operational simplicity, appreciable atom economy, short reaction time and easy purification procedure.

引用

页码：43881 / 43891

页数：11

共 50 条

[11] Synthesis and properties of cyanomethyl derivatives of imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, and imidazo[2,1-b]thiazole
Kutrov, G. P.
Kovalenko, N. V.
Volovenko, Yu. M.
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (02) : 257 - 262
[12] Synthesis and properties of cyanomethyl derivatives of imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, and imidazo[2,1-b]thiazole
G. P. Kutrov
N. V. Kovalenko
Yu. M. Volovenko
[J]. Russian Journal of Organic Chemistry, 2008, 44 : 257 - 262
[13] Formylation of furylsubstituted imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine and imidazo[2,2-b]thiazole
Saldabol, NO
Popelis, YY
Slavinskaya, VA
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2001, (08): : 1112 - 1115
[14] In(OTf)3 assisted synthesis of β-carboline C-3 tethered imidazo[1,2-a]azine derivatives
Devi, Nisha
Singh, Dharmender
Kaur, Gurpreet
Mor, Satbir
Putta, V. P. R. Kishore
Polina, Saibabu
Malakard, Chandi C.
Singh, Virender
[J]. NEW JOURNAL OF CHEMISTRY, 2017, 41 (03) : 1082 - 1093
[15] Synthesis of azepino[1,2-a]benzimidazoles and imidazo[1,2-a]azepines
Potikha L.M.
Turelyk A.R.
Kovtunenko V.A.
[J]. Chemistry of Heterocyclic Compounds, 2011, 47 (06) : 745 - 754
[16] Synthesis of imidazo[1,2-a] pyridine derivatives as antiviral agents
Mavel, S
Renou, JL
Galtier, C
Snoeck, R
Andrei, G
Balzarini, J
De Clercq, E
Gueiffier, A
[J]. ARZNEIMITTEL-FORSCHUNG-DRUG RESEARCH, 2001, 51 (04): : 304 - 309
[17] Design and synthesis of imidazo[1,2-a]pyridine-chalcone conjugates as antikinetoplastid agents
Agarwal, Devesh S.
Beteck, Richard M.
Ilbeigi, Kayhan
Caljon, Guy
Legoabe, Lesetja J.
[J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2024, 103 (01)
[18] NEW SYNTHESIS OF IMIDAZO[1,2-A]PYRIMIDINES AND PYRIMIDO[1,2-A]PYRIMIDINES
ABDELFATTAH, AM
SHERIF, SM
ELREEDY, AM
GADALLA, SA
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 70 (1-2) : 67 - 73
[19] ANTIULCER AGENTS .3. STRUCTURE ACTIVITY TOXICITY RELATIONSHIPS OF SUBSTITUTED IMIDAZO[1,2-A]PYRIDINES AND A RELATED IMIDAZO[1,2-A]PYRAZINE
KAMINSKI, JJ
PERKINS, DG
FRANTZ, JD
SOLOMON, DM
ELLIOTT, AJ
CHIU, PJS
LONG, JF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) : 2047 - 2051
[20] Regioselective synthesis of pyrrolo[1,2-a]-imidazoles and imidazo[1,2-a]-pyridines
Wang, Kai-Min
Ma, Yu-Lu
Lin, Xin-Rong
Yan, Sheng-Jiao
Lin, Jun
[J]. RSC ADVANCES, 2015, 5 (46): : 36472 - 36479

← 1 2 3 4 5 →