Tandem cyclization-[3+3] cycloaddition reactions of 2-alkynylbenzaldoxime: synthesis of fused 1,2-dihydroisoquinolines

被引：67
作者：
Ding, Qiuping [1 ,3 ]
Wang, Zhiyong [1 ]
Wu, Jie [1 ,2 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] Jiangxi Normal Univ, Analyt Ctr Phys & Chem, Nanchang 330027, Peoples R China
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 02期
基金：
中国国家自然科学基金;
关键词：
2-Alkynylbenzaldoxime; Dimethyl cyclopropane-1,1-dicarboxylate; 1,2-Dihydroisoquinoline; Silver triflate; Yetterbium triflate; CROSS-COUPLING REACTIONS; DIVERSITY-ORIENTED SYNTHESIS; ISOQUINOLINE-N-OXIDES; ORGANIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ELECTROPHILIC CYCLIZATION; ORGANOCATALYTIC ROUTE; NUCLEOPHILIC-ADDITION; DIPOLAR CYCLOADDITION;
D O I：
10.1016/j.tetlet.2008.10.121
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tandem cyclization-[3+3] cycloaddition of 2-alkynylbenzaldoximes with dimethyl cyclopropane-1,1-dicarboxylate co-catalyzed by AgOTf and Yb(OTf)(3) is described, which provides an useful method for the synthesis of tetrahydro-1,2-oxazine fused 1,2-dihydroisoquinolines. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：198 / 200
页数：3
相关论文
共 83 条
[1]   Synthesis of enantiopure carbohydrate mimetics by Lewis acid catalyzed rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines [J].
Al-Harrasi, A ;
Reissig, HU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6227-6231
[2]  
Arya P, 2001, ANGEW CHEM INT EDIT, V40, P339, DOI 10.1002/1521-3773(20010119)40:2<339::AID-ANIE339>3.0.CO
[3]  
2-J
[4]   Domino allylation and cyclization of ortho-alkynylbenzaldehydes with allyltrimethylsilane catalyzed by Pd(II)-Cu(II) bimetallic systems [J].
Asao, N ;
Chan, CS ;
Takahashi, K ;
Yamamoto, Y .
TETRAHEDRON, 2005, 61 (48) :11322-11326
[5]   Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines [J].
Asao, N ;
Yudha, S ;
Nogami, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5526-5528
[6]   An environmentally friendly synthetic method of 1,2-dihydroisoquinoline frameworks via three-component reaction with o-alkynylbenzaldehydes, primary amines, and pronucleophiles [J].
Asao, Naoki ;
Iso, Kentaro ;
Yudha S., Salprima .
ORGANIC LETTERS, 2006, 8 (18) :4149-4151
[7]  
Bentley K. W., 1998, The Isoquinoline Alkaloids, V1
[8]   Enantioselective synthesis of the pyrrolidine core of endothelin antagonist ABT-627 (Atrasentan) via 1,2-oxazines [J].
Buchholz, M ;
Reissig, HU .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (18) :3524-3533
[9]   Total synthesis of (+)-phyllantidine [J].
Carson, Cheryl A. ;
Kerr, Michael A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6560-6563
[10]   Synthesis of (+)-CP-263,114 [J].
Chen, C ;
Layton, ME ;
Sheehan, SM ;
Shair, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7424-7425
123456789