Synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones involving one-pot three-component tandem Knoevenagel-Michael reaction catalyzed by n-tetrabutylammonium tribromide (TBATB)

被引：19

作者：

Ghosh, Arindam ^{[1
]}

Khan, Abu T. ^{[1
,2
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

[2] Aliah Univ, Kolkata 700091, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 12期

关键词：

Multicomponent reactions; 4-Hydroxycoumarin; Aldehydes; 3-Amino-5-methyl-pyrazole; n-Tetrabutylammonium tribromide (TBATB); Dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-one derivatives; ENVIRONMENTALLY BENIGN SYNTHESIS; MULTICOMPONENT REACTIONS; AMMONIUM TRIBROMIDE; CARBONYL-COMPOUNDS; ATOM ECONOMY; CONDENSATION; CLEAVAGE;

D O I：

10.1016/j.tetlet.2014.02.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones was achieved through one-pot three-component reaction from 4-hydroxycoumarin, aldehydes, and 3-amino-5-methyl-pyrazole in acetonitrile using 5 mol % TBATB as the catalyst under reflux condition. The product formation is through tandem Knoevenagel-Michael reaction followed by concomitant cyclization. Simple reaction procedure, shorter reaction time, good yields, avoidance of aqueous work-up, and column chromatographic separation are some of the salient features of the present protocol. (c) 2014 Elsevier Ltd. All rights reserved.

引用

页码：2006 / 2009

页数：4

共 26 条

[1] Molecular iodine catalyzed one-pot multicomponent reactions for the synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones
Pal, Suman
Khan, Md. Nasim
Karamthulla, Shaik
Choudhury, Lokman H.
RSC ADVANCES, 2013, 3 (36): : 15705 - 15711
[2] Three-component one-pot synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridines
Sadat-Ebrahimi, Seyed Esmail
Katebi, Shirin
Pirali-Hamedani, Morteza
Moghimi, Setareh
Yahya-Meymandi, Azadeh
Mahdavi, Mohammad
Shafiee, Abbas
Foroumadi, Alireza
HETEROCYCLIC COMMUNICATIONS, 2016, 22 (04) : 247 - 250
[3] An Efficient One-Pot Green Protocol for the Synthesis of Dihydrochromeno[4,3-b]Pyrazolo[4,3-e]Pyridin-6(7H)-Ones Mediated by Diisopropyl Ethyl Ammonium Acetate at Room Temperature
Kulkarni, Makrand, V
Jadhav, Chetan K.
Nipate, Amol S.
Bhutada, Sarita, V
Gill, Charansingh H.
Magar, Bhausaheb K.
POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (08) : 7223 - 7237
[4] Crystal structure of 7-phenyl-9,11-dihydrochromeno-(4,3-b)pyrazolo(4,3-e)pyridine-6(7H)-one
Platonova, A. G.
Mazhukina, O. A.
Fedotova, O. V.
JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 56 (06) : 1205 - 1208
[5] Crystal structure of 7-phenyl-9,11-dihydrochromeno-(4,3-b)pyrazolo(4,3-e)pyridine-6(7H)-one
A. G. Platonova
O. A. Mazhukina
O. V. Fedotova
Journal of Structural Chemistry, 2015, 56 : 1205 - 1208
[6] One-Pot Three-Component Synthesis of Pyrano [3,2-b]pyrazolo[4,3-e]pyridin-8(1H)-ones
Safaei, Shirin
Mohammadpoor-Baltork, Iraj
Khosropour, Ahmad Reza
Moghadam, Majid
Tangestaninejad, Shahram
Mirkhani, Valiollah
Khavasi, Hamid Reza
ACS COMBINATORIAL SCIENCE, 2013, 15 (03) : 141 - 146
[7] Synthesis of 4-aryl-1-ethyl-7-methyl-1,9-dihydropyrano[4,3-b]pyrazolo[4,3-e]pyridin-5(4H)-one via a three-component condensation
Hassanabadi, Alireza
Khandan-Barani, Khatereh
Saffari, Jilla
JOURNAL OF CHEMICAL RESEARCH, 2016, (09) : 576 - 578
[8] Synthesis and Crystal Structure of 8-Methyl-7-(3-nitrophenyl)-10-phenyl-10,11-dihydrochromeno[4, 3-b]pyrazolo[4,3-e]pyridin-6-(7H)-one
Lin Zhi-Lan
You Xin-Kui
Zhang Xue-Li
Gao Yuan
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2012, 31 (01) : 57 - 60
[9] Synthesis and Crystal Structure of 8-Methyl-7-(3-nitrophenyl)-10-phenyl-10,11-dihydrochro-meno[4,3-b]pyrazolo[4,3-e]pyridin-6-(7H)-one
林志兰
游新奎
张雪利
高原
结构化学, 2012, 31 (01) : 57 - 60
[10] Reaction of Imidoformates with Anthranilates: Facile, One-Pot, Three-Component Synthesis of 8H-Quinazolino[4,3-b]quinazolin-8-ones
Venkateswarlu, S.
Satyanarayana, M.
Ravikiran, P.
Siddaiah, V.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) : 1089 - 1093

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