Palladium-Catalyzed Three-Component Reaction of 2,3-Allenyl Amines, Isocyanates, and Organic Halides: A Diversified Assembly of Imidazolidinones

被引:15
作者
Shu, Wei [3 ]
Yu, Qiong [2 ]
Jia, Guochen [1 ]
Ma, Shengming [2 ,3 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
allenes; amines; cyclization; heterocycles; isocyanates; palladium; CGRP RECEPTOR ANTAGONISTS; CYCLIC UREA DERIVATIVES; MULTICOMPONENT REACTIONS; STEREOSELECTIVE SYNTHESIS; 2+2+2 CYCLOADDITION; EFFICIENT SYNTHESIS; INSERTION REACTIONS; HETEROCYCLES; INHIBITORS; IMIDAZOLONES;
D O I
10.1002/chem.201003611
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A three-component reaction of 2,3-allenyl amines with isocyanates and organic halides has been developed. Two carbon-nitrogen bonds as well as a carbon-carbon bond were sequentially formed to construct imidazolidinone derivatives in good to excellent yields (see scheme). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:4720 / 4723
页数:4
相关论文
共 60 条
[1]   Efficient synthesis of diastereomerically pure vicinal diamines: meso-2,3-bis(methylamino)butane and cis-1,2-bis(methylamino)cycloalkanes [J].
Akester, J ;
Cui, JJ ;
Fraenkel, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :431-434
[2]  
[Anonymous], 1977, ANGEW CHEM
[3]   Insertion reactions of allenes with transition metal complexes [J].
Bai, Tao ;
Ma, Shengming ;
Jia, Guochen .
COORDINATION CHEMISTRY REVIEWS, 2009, 253 (3-4) :423-448
[4]   GASTRIC ANTISECRETORY AGENTS .1. ANTISECRETORY AND ANTI-ULCER ACTIVITY OF 5H-[1]BENZOPYRANO[2,3-B]PYRIDIN-5-YLUREAS AND 5H-[1]BENZOTHIOPYRANO[2,3-B]PYRIDIN-5-YLUREAS [J].
BRISTOL, JA ;
GOLD, EH ;
LOVEY, RG ;
LONG, JF .
JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (08) :927-932
[5]   Discovery of the first antibacterial small molecule inhibitors of MurB [J].
Bronson, JJ ;
DenBleyker, KL ;
Falk, PJ ;
Mate, RA ;
Ho, HT ;
Pucci, MJ ;
Snyder, LB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (05) :873-875
[6]   Benzodiazepine calcitonin gene-related peptide (CGRP) receptor antagonists: Optimization of the 4-substituted piperidine [J].
Burgey, Christopher S. ;
Stump, Craig A. ;
Nguyen, Diem N. ;
Deng, James Z. ;
Quigley, Amy G. ;
Norton, Beth R. ;
Bell, Ian M. ;
Mosser, Scott D. ;
Salvatore, Christopher A. ;
Rutledge, Ruth Z. ;
Kane, Stefanie A. ;
Koblan, Kenneth S. ;
Vacca, Joseph P. ;
Graham, Samuel L. ;
Williams, Theresa M. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) :5052-5056
[7]   1-(3-cyanobenzylpiperidin-4-yl)-5-methyl-4-phenyl-1,3-dihydroimidazol-2-one:: A selective high-affinity antagonist for the human dopamine D4 receptor with excellent selectivity over ion channels [J].
Carling, RW ;
Moore, KW ;
Moyes, CR ;
Jones, EA ;
Bonner, K ;
Emms, F ;
Marwood, R ;
Patel, S ;
Patel, S ;
Fletcher, AE ;
Beer, M ;
Sohal, B ;
Pike, A ;
Leeson, PD .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (14) :2706-2715
[8]   Synthesis of axinohydantoins [J].
Carolina, A ;
Sosa, B ;
Yakushijin, K ;
Horne, DA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4498-4500
[9]  
CHAWLA HM, 1990, TETRAHEDRON, V46, P1331
[10]   Design, synthesis, and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2-thione analogues [J].
Congiu, Cenzo ;
Cocco, Maria Teresa ;
Onnis, Valentina .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :989-993