A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives

被引：10

作者：

Cai, Qun ^{[1
]}

Zhu, Yan-Ping ^{[1
]}

Gao, Yang ^{[1
]}

Sun, Jing-Jing ^{[1
]}

Wu, An-Xin ^{[1
]}

机构：

[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2013年 / 91卷 / 06期

基金：

美国国家科学基金会;

关键词：

indolizine derivative; iodination; pyridinium ylide synthesis; 1; 3-dipolar cycloaddition; tandem synthesis; NITROGEN-BRIDGED HETEROCYCLES; QUINOLIZIDINE ALKALOIDS; FACILE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; INTEGRATION; ANNULATION; EFFICIENT; ALKENES; YLIDES; INDOLE;

D O I：

10.1139/cjc-2012-0534

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylide synthesis, and 1,3- dipolar cycloaddition. The protocols were found to be highly efficient in terms of high yields, operational simplicity, mild reaction conditions, and easy workup. This method has provided an important supplement for the synthesis of indolizine derivatives via a novel tandem synthesis.

引用

页码：414 / 419

页数：6

共 51 条

[1] Multiple-component condensation strategies for combinatorial library synthesis
Armstrong, RW
Combs, AP
Tempest, PA
Brown, SD
Keating, TA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) : 123 - 131
[2] 1-Benzopyran-4(4H)-ones as novel activated alkenes in the Baylis-Hillman reaction:: a simple and facile synthesis of indolizine-fused-chromones
Basavaiah, D
Rao, AJ
[J]. TETRAHEDRON LETTERS, 2003, 44 (23) : 4365 - 4368
[3] The Baylis-Hillman Bromides as Versatile Synthons: A Facile One-Pot Synthesis of Indolizine and Benzofused Indolizine Frameworks
Basavaiah, Deevi
Devendar, Badugu
Lenin, Dandamudi V.
Satyanarayana, Tummanapalli
[J]. SYNLETT, 2009, (03) : 411 - 416
[4] Boekelheide V., 1959, J AM CHEM SOC, V81, P56
[5] A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction
Bora, U
Saikia, A
Boruah, RC
[J]. ORGANIC LETTERS, 2003, 5 (04) : 435 - 438
[6] THE CHEMISTRY OF THE PYRROCOLINES AND THE OCTAHYDROPYRROCOLINES
BORROWS, ET
HOLLAND, DO
[J]. CHEMICAL REVIEWS, 1948, 42 (03) : 611 - 643
[7] Boultadakis E, 2002, SYNLETT, P1547
[8] Non-imidazole heterocyclic histamine H3 receptor antagonists
Chai, WY
Breitenbucher, JG
Kwok, A
Li, XB
Wong, V
Carruthers, NI
Lovenberg, TW
Mazur, C
Wilson, SJ
Axe, FU
Jones, TK
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (10) : 1767 - 1770
[9] Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine
Chernyak, Natalia
Tilly, David
Li, Zhou
Gevorgyan, Vladimir
[J]. ARKIVOC, 2011, : 76 - 91
[10] Synthesis of Decahydropyrrolo[2,1,5-cd]indolizine through Consecutive [2+3] Cycloadditions and 6-Exo-Trig Cyclization
Cui, Peipei
Xu, Liang
Shi, Zhangjie
Gan, Liangbing
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) : 4210 - 4212

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