SULFAMIC ACID CATALYZED FIVE COMPONENT REACTION FOR EFFICIENT AND ONE-POT SYNTHESIS OF DENSELY FUNCTIONALIZED TETRAHYDROPYRIDINE SCAFFOLD

被引：6

作者：

Sarkate, Aniket P. ^{[1
]}

Sangshetti, Jaiprakash N. ^{[2
]}

Dharbale, Nanasaheb B. ^{[1
]}

Sarkate, Ajinkya P. ^{[3
]}

Shinde, Devanand B. ^{[1
]}

机构：

[1] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem Technol, Aurangabad, Maharashtra, India

[2] YB Chavan Coll Pharm, Dept Pharmaceut Chem, Aurangabad, Maharashtra, India

[3] Bharati Vidyapeeth, Poona Coll Pharm, Dept Pharmaceut Chem, Pune, Maharashtra, India

来源：

JOURNAL OF THE CHILEAN CHEMICAL SOCIETY | 2015年 / 60卷 / 01期

关键词：

Sulfamic acid; functionalized tetrahydropyridines; one-pot; five component reaction; MULTICOMPONENT REACTIONS; CONCISE SYNTHESIS; PIPERIDINES; ATOM;

D O I：

10.4067/S0717-97072015000100012

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The utility of sulfamic acid in One-pot assembling of aromatic aldehydes, aromatic amines and beta-keto esters to afford densely functionalized tetrahydropyridines in 70-89% yield has been presented. The advantage of sulfamic acid against other catalysts in terms of yield has been studied. The effect of different solvents on reaction time and yield has also been studied. Easy work up and mild reaction condition are the advantages of the proposed method.

引用

页码：2832 / 2836

页数：5

共 29 条

[1] Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction
Balan, D
Adolfsson, H
[J]. TETRAHEDRON LETTERS, 2003, 44 (12) : 2521 - 2524
[2] Efficient preparation of the isoindoline framework via a six component, tandem double A3-coupling and [2+2+2] cycloaddition reaction
Bonfield, E. Ryan
Li, Chao-Jun
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) : 370 - 374
[3] Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature
Brahmachari, Goutam
Das, Suvankar
[J]. TETRAHEDRON LETTERS, 2012, 53 (12) : 1479 - 1484
[4] Iron(III)-promoted aza-prins-cyclization:: Direct synthesis of six-membered azacycles
Carballo, Ruben M.
Ramirez, Miguel A.
Rodriguez, Matias L.
Martin, Victor S.
Padron, Juan I.
[J]. ORGANIC LETTERS, 2006, 8 (17) : 3837 - 3840
[5] Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation
Clarke, Paul A.
Zaytzev, Andrey V.
Whtwoo, Adrian C.
[J]. TETRAHEDRON LETTERS, 2007, 48 (30) : 5209 - 5212
[6] Alkaloids from amphibian skin: A tabulation of over eight-hundred compounds
Daly, JW
Spande, TF
Garraffo, HM
[J]. JOURNAL OF NATURAL PRODUCTS, 2005, 68 (10): : 1556 - 1575
[7] Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer
Davis, FA
Chao, B
Rao, A
[J]. ORGANIC LETTERS, 2001, 3 (20) : 3169 - 3171
[8] The Efficient One-Pot Reaction of up to Eight Components by the Union of Multicomponent Reactions
Elders, Niels
van der Born, Dion
Hendrickx, Loes J. D.
Timmer, Brian J. J.
Krause, Alrik
Janssen, Elwin
de Kanter, Frans J. J.
Ruijter, Eelco
Orru, Romano V. A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (32) : 5856 - 5859
[9] New three-component reaction:: Novel formation of a seven-membered ring by the unexpected reaction at the γ-position of the β-keto ester
Fujioka, Hiromichi
Murai, Kenichi
Kubo, Ozora
Ohba, Yusuke
Kita, Yasuyuki
[J]. ORGANIC LETTERS, 2007, 9 (09) : 1687 - 1690
[10] Enantioselective organocatalytic intramolecular aza-Michael reaction:: a concise synthesis of (+)-sedamine., (+)-allosedamine, and (+)-coniine
Fustero, Santos
Jimenez, Diego
Moscardo, Javier
Catalan, Silvia
del Pozo, Carlos
[J]. ORGANIC LETTERS, 2007, 9 (25) : 5283 - 5286

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