Convergent synthesis of azabicycloalkenones using squaric acid as platform

被引：29

作者：

Yamamoto, Yoshihiko

Kuwabara, Shoji

Hayashi, Hiroki

Nishiyama, Hisao

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

[2] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 16-17期

关键词：

C-C activation; cycloaddition; heterocycles; rhodium; small ring systems;

D O I：

10.1002/ADSC.200606097

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of azabicycloalkenones bearing a vinylogous amide moiety was achieved by means of the rhodium-catalyzed decarbonylative cycloaddition of cyclobutenediones with a pendant alkene. The starting cyclobutenediones were efficiently prepared from appropriate squaric acid monoesters and N-benzylalkenylamines under microwave heating conditions.

引用

页码：2493 / 2500

页数：8

共 55 条

[21] The rhodium-catalyzed Pauson-Khand reaction
Kobayashi, T
Koga, Y
Narasaka, K
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 73 - 87
[22] Koga Y, 1998, CHEM LETT, P249
[23] Ru- and Rh-catalyzed C-C bond cleavage of cyclobutenones: Reconstructive and selective synthesis of 2-pyranones, cyclopentenes, and cyclohexenones
Kondo, T
Taguchi, Y
Kaneko, Y
Niimi, M
Mitsudo, TA
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (40) : 5369 - 5372
[24] Rapid ruthenium-catalyzed synthesis of pyranopyrandiones by reconstructive carbonylation of cyclopropenones involving C-C bond cleavage
Kondo, T
Kaneko, Y
Taguchi, Y
Nakamura, A
Okada, T
Shiotsuki, M
Ura, Y
Wada, K
Mitsudo, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) : 6824 - 6825
[25] Ruthenium-catalyzed reconstructive synthesis of cyclopentenones by unusual coupling of cyclobutenediones with alkenes involving carbon-carbon bond cleavage
Kondo, T
Nakamura, A
Okada, T
Suzuki, N
Wada, K
Mitsudo, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) : 6319 - 6320
[26] KONDO T, 2005, ANGEW CHEM, V116, P5483
[27] SYNTHESIS AND REACTIVITY OF CAPTODATIVE CYANOKETENES
LABILLE, MC
JANOUSEK, Z
VIEHE, HG
[J]. TETRAHEDRON, 1991, 47 (38) : 8161 - 8166
[28] Regioselectivity, stereoselectivity and catalysis in intermolecular Pauson-Khand reactions: Teaching an old dog new tricks
Laschat, S
Becheanu, A
Bell, T
Baro, A
[J]. SYNLETT, 2005, (17) : 2547 - 2570
[29] CYCLOBUTENEDIONES AS PRECURSORS TO QUINONES AND CYCLOPENTENONES
LIEBESKIND, LS
[J]. TETRAHEDRON, 1989, 45 (10) : 3053 - 3060
[30] AN IMPROVED METHOD FOR THE SYNTHESIS OF SUBSTITUTED CYCLOBUTENEDIONES
LIEBESKIND, LS
FENGL, RW
WIRTZ, KR
SHAWE, TT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) : 2482 - 2488

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