Cascade Coupling/Cyclization process to n-substituted 1,3-dihydrobenzimidazol-2-ones

被引:85
作者
Zou, Benli
Yuan, Offlang
Ma, Dawei [1 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan, Nat Prod Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ol701792j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Assembly of N-substituted 1,3-dihydrobenzimidazol-2-ones is achieved starting from methyl o-haloarylcarbamates via a Cul/amino acid catalyzed coupling with amines and subsequent condensative cyclization. A number of functional groups are tolerated by these reaction conditions, including vinyl, nitro, carboxylate, amide, ester, ketone, and silyl ether groups.
引用
收藏
页码:4291 / 4294
页数:4
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共 37 条
[1]   A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles [J].
Altenhoff, G ;
Glorius, F .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1661-1664
[2]   The copper-catalyzed N-arylation of indoles [J].
Antilla, JC ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688
[3]   Computational strategies in discovering novel non-nucleoside inhibitors of HIV-1 RT [J].
Barreca, ML ;
Rao, A ;
De Luca, L ;
Zappalà, L ;
Monforte, AM ;
Maga, G ;
Pannecouque, C ;
Balzarini, J ;
De Clercq, E ;
Chimirri, A ;
Monforte, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) :3433-3437
[4]   Identification of novel, orally bioavailable spirohydantoin CGRP receptor antagonists [J].
Bell, Ian M. ;
Bednar, Rodney A. ;
Fay, John F. ;
Gallicchio, Steven N. ;
Hochman, Jerome H. ;
McMasters, Daniel R. ;
Miller-Stein, Cynthia ;
Moore, Eric L. ;
Mosser, Scott D. ;
Pudvah, Nicole T. ;
Quigley, Amy G. ;
Salvatore, Christopher A. ;
Stump, Craig A. ;
Theberge, Cory R. ;
Wong, Bradley K. ;
Zartman, C. Blair ;
Zhang, Xu-Fang ;
Kane, Stefanie A. ;
Graham, Samuel L. ;
Vacca, Joseph P. ;
Williams, Theresa M. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (24) :6165-6169
[5]   Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions [J].
Cai, Q ;
Zhu, W ;
Zhang, H ;
Zhang, YD ;
Ma, DW .
SYNTHESIS-STUTTGART, 2005, (03) :496-499
[6]   Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622
[7]   Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides [J].
Evindar, G ;
Batey, RA .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :1802-1808
[8]   Copper- and palladium-catalyzed intramolecular aryl guanidinylation: An efficient method for the synthesis of 2-aminobenzimidazoles [J].
Evindar, G ;
Batey, RA .
ORGANIC LETTERS, 2003, 5 (02) :133-136
[9]   Piperidine amides as 11β-hydroxysteroid dehydrogenase type 1 inhibitors [J].
Flyren, Katarina ;
Bergquist, Lars O. ;
Castro, Victor M. ;
Fotsch, Christopher ;
Johansson, Lars ;
Jean, David J. St., Jr. ;
Sutin, Lori ;
Williams, Meredith .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (12) :3421-3425
[10]   Ligand-accelerated catalysis of the Ullmann condensation: Application to hole conducting triarylamines [J].
Goodbrand, HB ;
Hu, NX .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :670-674