PhI(OAc)2-mediated novel 1,3-dipolar cycloaddition of methylenecyclopropanes (MCPs), vinylidenecyclopropanes (VCPs), and methylenecyclobutane (MCB) with phthalhydrazide

被引：80
作者：
Liu, Le-Ping [1 ]
Lu, Jian-Mei [1 ]
Shi, Min [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 07期
关键词：
D O I：
10.1021/ol070178r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Iodobenzene diacetate-mediated reactions of methylenecyclopropanes 1, vinylidenecyclopropanes 2, and a methylenecyclobutane 3a with phthalhydrazide give the corresponding [3+2] cycloaddition products in good yields under mild conditions. In these reactions, phthalhydrazide was transformed to a 1,3-dipole intermediate in the presence of iodobenzene diacetate. A plausible reaction mechanism has been proposed.
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页码：1303 / 1306
页数：4
相关论文
共 56 条
[1]  
Binger P, 1998, EUR J ORG CHEM, V1998, P113
[2]   Synthesis of methylene- and alkylidenecyclopropane derivatives [J].
Brandi, A ;
Goti, A .
CHEMICAL REVIEWS, 1998, 98 (02) :589-635
[3]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269
[4]   Ceric(IV)-mediated reaction of methylenecyclopropanes in organic synthesis: A facile access to dihydrofurans and cyclobutanones [J].
Chen, WL ;
Huang, M ;
Zhou, HW ;
Ren, LJ .
SYNTHESIS-STUTTGART, 2006, (04) :609-614
[5]  
CONTRERAS FG, 1987, HETEROCYCLES, V25, P193
[6]  
CONTRERAS FG, 1989, HETEROCYCLES, V28, P791
[7]   Novel prospects of the acidic thermal rearrangement of spiro[cyclopropane-1,5′-isoxazolidines] to β-lactams [J].
Cordero, FM ;
Salvati, M ;
Pisaneschi, F ;
Brandi, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (10) :2205-2213
[8]   PI-FACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF HEXACYCLO[10.2.1.0(2,11).0(4,9).0(4,14).0(9,13)]PENTADECA-5,7-DIENE-3,10-DIONE [J].
COXON, JM ;
OCONNELL, MJ ;
STEEL, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4726-4732
[9]   Intramolecular Pauson-Khand reactions of methylenecyclopropane and bicyclopropylidene derivatives as an approach to spiro(cyclopropanebicyclo[n.3.0]alkenones) [J].
de Meijere, A ;
Becker, H ;
Stolle, A ;
Kozhushkov, SI ;
Bes, MT ;
Salaün, J ;
Noltemeyer, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2471-2482
[10]  
de Meijere A, 2000, TOP CURR CHEM, V207, P89
123456