1,4-Dipolar Cycloaddition Reactions in Ionic Liquids: A Facile Synthesis of 9aH,15H-[1]Benzopyrano[3′,2′:3,4]pyrido[2,1-a]isoquinolines (=9aH,15H-Benzo[a][1]benzopyrano[2,3-h]quinolizines)

被引：6

作者：

Reddy, Basi V. Subba ^{[1
]}

Yadav, Nagendra Nath ^{[1
]}

Srivastava, Nikhil ^{[1
]}

Yadav, Jhillu S. ^{[1
]}

Sridhar, Balasubramanian ^{[2
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Ctr Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

来源：

HELVETICA CHIMICA ACTA | 2012年 / 95卷 / 01期

关键词：

1]Benzopyranopyrido-isoquinolines; Benzo-[1]benzopyrano-quinolizines; Cycloadditions; X-Ray crystallography; Ionic liquids; Multicomponent reactions; QUINOLINE-DMAD ZWITTERION; DIMETHYL ACETYLENEDICARBOXYLATE; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; ENANTIOSELECTIVE ADDITION; STEREOSELECTIVE-SYNTHESIS; ACTIVATED ACETYLENES; N-HETEROCYCLES; ISOQUINOLINE; CONSTRUCTION;

D O I：

10.1002/hlca.201100250

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ionic liquids were found to be a suitable reaction medium for 1,4-dipolar cycloaddition reactions of an isoquinoline, an activated alkyne, and a 4-oxo-4H-1-benzopyran-3-carboxaldehyde at room temperature to afford [1]benzopyrano-pyrido-isoquinoline (=9aH,15H-benzo[a][1]benzopyrano[2,3-h]quinolizine) derivatives selectively in good yields. The ionic liquid can be recovered and recycled in further runs without loss of activity.

引用

页码：76 / 86

页数：11

共 60 条

[1] Enantioselective addition of organolithium reagents on isoquinoline
Alexakis, A
Amiot, F
[J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (19) : 2117 - 2122
[2] 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
[3] Pd-assisted multicomponent synthesis of heterocycles
Balme, G
Bossharth, E
Monteiro, N
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) : 4101 - 4111
[4] STUDIES ON SRN1 REACTIONS-9 - A NEW ACCESS TO THE ISOQUINOLINE RING-SYSTEM
BEUGELMANS, R
CHASTANET, J
ROUSSI, G
[J]. TETRAHEDRON, 1984, 40 (02) : 311 - 314
[5] Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6] 2-A
[7] Total synthesis of cribrostatin IV: Fine-tuning the character of an amide bond by remote control
Chan, C
Heid, R
Zheng, SP
Guo, JS
Zhou, BS
Furuuchi, T
Danishefsky, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4596 - 4598
[8] A facile preparation of benzyltrimethylstannanes and their utility in the synthesis of 1-benzyl-1,2-dihydroisoquinolines
Deline, JE
Miller, RB
[J]. TETRAHEDRON LETTERS, 1998, 39 (13) : 1721 - 1724
[9] N-acylazinium salts: A new source of iminium ions for Ugi-type processes
Diaz, JL
Miguel, M
Lavilla, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) : 3550 - 3553
[10] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

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