A one-pot synthesis of substituted pyrido[2,3-b]indolizines

被引：13

作者：

Proenca, Fernanda ^{[1
]}

Costa, Marta ^{[1
]}

机构：

[1] Univ Minho, Dept Chem, P-4710057 Braga, Portugal

来源：

TETRAHEDRON | 2011年 / 67卷 / 06期

关键词：

1-(Cyanomethyl)pyridinium chloride; Acetylacetone; alpha; beta-unsaturated carbonyl compounds; Pyrido[2,3-b]indolizine; One-pot synthesis; INDOLIZINE DERIVATIVES; INHIBITORS;

D O I：

10.1016/j.tet.2010.12.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and novel approach to the synthesis of substituted pyrido[2,3-b]indolizine-10-carbonitriles was developed. These structures are practically unavailable through previously described methods. The cascade transformation involves the reaction of alpha,beta-unsaturated carbonyl compounds with a stable dimer prepared from 1-(cyanomethyl)pyridinium chloride. The reaction was performed under reflux conditions in ethanol/water and in the presence of sodium acetate. This procedure represents a eco-friendly regioselective approach to the pyrido[2,3-b]indolizine core structure. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1071 / 1075

页数：5

共 17 条

[1] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
Asano, N
Nash, RJ
Molyneux, RJ
Fleet, GWJ
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (08) : 1645 - 1680
[2] SYNTHESIS OF NEW HETEROCYCLIC RING-SYSTEMS - INDENO[2,1-B]-BENZO[G]INDOLIZINE AND INDENO[1',2'-5,4]PYRROLO[2,1-A]PHTHALAZINE
CAMPAGNA, F
CAROTTI, A
CASINI, G
MACRIPO, M
[J]. HETEROCYCLES, 1990, 31 (01) : 97 - 107
[3] Key green chemistry research areas - a perspective from pharmaceutical manufacturers
Constable, David J. C.
Dunn, Peter J.
Hayler, John D.
Humphrey, Guy R.
Leazer, Johnnie L., Jr.
Linderman, Russell J.
Lorenz, Kurt
Manley, Julie
Pearlman, Bruce A.
Wells, Andrew
Zaks, Aleksey
Zhang, Tony Y.
[J]. GREEN CHEMISTRY, 2007, 9 (05) : 411 - 420
[4] Potent, selective and cell-mediated inhibition of human herpesvirus 6 at an early stage of viral replication by the non-nucleoside compound CMV423
De Bolle, L
Andrei, G
Snoeck, R
Zhang, Y
Van Lommel, A
Otto, M
Bousseau, A
Roy, C
De Clercq, E
Naesens, L
[J]. BIOCHEMICAL PHARMACOLOGY, 2004, 67 (02) : 325 - 336
[5] Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis
Gundersen, Lise-Lotte
Charnock, Colin
Negussie, Ayele Hailu
Rise, Frode
Teklu, Solomon
[J]. EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2007, 30 (01) : 26 - 35
[6] Indolizines as novel potent inhibitors of 15-lipoxygenase
Gundersen, LL
Malterud, KE
Negussie, AH
Rise, F
Teklu, S
Ostby, OB
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (24) : 5409 - 5415
[7] PREPARATION OF NEW NITROGEN-BRIDGED HETEROCYCLES. 64. A SMOOTH FORMATION OF 2,4-DIARYLPYRIDO[2,3-b]INDOLIZINE-10-CARBONITRILE DERIVATIVES
Kakehi, Akikazu
Suga, Hiroyuki
Sato, Shuichi
[J]. HETEROCYCLES, 2009, 77 (01) : 471 - 481
[8] KATRITZKY AR, 1996, COMPREHENSIVE HETERO, V8, P237
[9] Kitadokoro K, 1998, J BIOCHEM, V123, P619
[10] Lide D.R., 1995, CRC HDB CHEM PHYS, V76th, P1

← 1 2 →