Synthesis of highly functionalized piperidines by one-pot multicomponent reaction using tetrabutylammonium tribromide (TBATB)

被引：158

作者：

Khan, Abu T. ^{[1
]}

Lal, Mohan ^{[1
]}

Khan, Md Musawwer ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 33期

关键词：

TBATB; Heterocycles; Piperidines; Multicomponent reactions; 1,3-Dicarbonyl compounds; EFFICIENT CHEMOSELECTIVE REAGENT; ENVIRONMENTALLY BENIGN SYNTHESIS; DIELS-ALDER REACTION; CYCLIZATION REACTIONS; CARBONYL-COMPOUNDS; CONCISE SYNTHESIS; DERIVATIVES; EXPEDIENT; ATOM; INHIBITORS;

D O I：

10.1016/j.tetlet.2010.06.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrabutylammonium tribromide (TBATB) has been found to be an efficient catalyst for the one-pot synthesis of highly substituted piperidines through a combination of 1,3-dicarbonyl compounds, aromatic aldehydes, and various amines in ethanol at room temperature Atom economy. good yields, environmentally benign. and mild reaction conditions are some of the important features of this protocol (C) 2010 Elsevier Ltd All rights reserved

引用

页码：4419 / 4424

页数：6

共 52 条

[1] Highly enantioselective dynamic kinetic resolution and desymmetrization processes by cyclocondensation of chiral aminoalcohols with racemic or prochiral δ-oxoacid derivatives
Amat, M
Bassas, O
Pericàs, MA
Pastó, M
Bosch, J
[J]. CHEMICAL COMMUNICATIONS, 2005, (10) : 1327 - 1329
[2] MASTERING BETA-KETO-ESTERS
BENETTI, S
ROMAGNOLI, R
DERISI, C
SPALLUTO, G
ZANIRATO, V
[J]. CHEMICAL REVIEWS, 1995, 95 (04) : 1065 - 1114
[3] An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n-tetrabutylammonium tribromide
Bose, G
Mondal, E
Khan, AT
Bordoloi, MJ
[J]. TETRAHEDRON LETTERS, 2001, 42 (50) : 8907 - 8909
[4] A convenient and useful method of preparation of α-bromo enones from the corresponding enones using organic ammonium tribromide (OATB)
Bose, G
Barua, PMB
Chaudhuri, MK
Kalita, D
Khan, AT
[J]. CHEMISTRY LETTERS, 2001, (04) : 290 - 291
[5] 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
[6] An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB)
Chaudhuri, MK
Khan, AT
Patel, BK
Dey, D
Kharmawophlang, W
Lakshmiprabha, TR
Mandal, GC
[J]. TETRAHEDRON LETTERS, 1998, 39 (44) : 8163 - 8166
[7] 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
[8] 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
[9] 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
[10] Rapid access to trans-2,6-disubstituted piperidines:: Expedient total syntheses of (-)-solenopsin A and (+)-epi-dihydropinidine
Dobbs, AP
Guesné, SJJ
[J]. SYNLETT, 2005, (13) : 2101 - 2103

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