A one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles

被引:65
作者
Cee, Victor J. [1 ]
Downing, Nicholas S. [1 ]
机构
[1] Amgen Inc, Chem Res & Discovery, Cambridge, MA 02139 USA
关键词
aminobenzimidazole; cyclodesulfurization; polymer-supported carbodiimide;
D O I
10.1016/j.tetlet.2006.03.112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rapid and efficient one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles is described. The reaction is mediated by a polymer-supported carbodiimide, which simplifies product isolation. The scope and limitations of this method are described. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3747 / 3750
页数:4
相关论文
共 33 条
[21]  
OMAR AMME, 1976, PHARMAZIE, V31, P348
[22]   CYCLODESULFURIZATION OF THIO COMPOUNDS .16. DICYCLOHEXYLCARBODIIMIDE AS AN EFFICIENT CYCLODESULFURIZING AGENT IN SYNTHESIS OF HETEROCYCLIC-COMPOUNDS FROM VARIOUS THIO COMPOUNDS [J].
OMAR, AMME ;
HABIB, NS ;
ABOULWAFA, OM .
SYNTHESIS-STUTTGART, 1977, (12) :864-865
[23]   Utility of complementary molecular reactivity and molecular recognition (CMR/R) technology and polymer-supported reagents in the solution-phase synthesis of heterocyclic carboxamides [J].
Parlow, JJ ;
Mischke, DA ;
Woodard, SS .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5908-5919
[24]   Synthesis of 2-(alkylamino)benzimidazoles [J].
Perkins, JJ ;
Zartman, AE ;
Meissner, RS .
TETRAHEDRON LETTERS, 1999, 40 (06) :1103-1106
[25]  
RAM S, 1984, HETEROCYCLES, V22, P1789
[26]   Discovery of 2-phenylamino-imidazo[4,5-h]isoquinolin-9-ones: A new class of inhibitors of lck kinase [J].
Snow, RJ ;
Cardozo, MG ;
Morwick, TM ;
Busacca, CA ;
Dong, Y ;
Eckner, RJ ;
Jacober, S ;
Jakes, S ;
Kapadia, S ;
Lukas, S ;
Panzenbeck, M ;
Peet, GW ;
Peterson, JD ;
Prokopowicz, AS ;
Sellati, R ;
Tolbert, RM ;
Tschantz, MA ;
Moss, N .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (16) :3394-3405
[27]   Isoquinolinone synthesis by SNAr reaction:: a versatile route to imidazo[4,5-h]isoquinolin-9-ones [J].
Snow, RJ ;
Butz, T ;
Hammach, A ;
Kapadia, S ;
Morwick, TM ;
Prokopowicz, AS ;
Takahashi, H ;
Tan, JD ;
Tschantz, MA ;
Wang, XJ .
TETRAHEDRON LETTERS, 2002, 43 (42) :7553-7556
[28]   SELECTIVE AND EFFICIENT SYNTHESES OF PERHYDRO-1,3,5-TRIAZINE-2,4,6-TRIONES AND CARBODIIMIDES FROM ISOCYANATES USING ZP(MENCH(2)CH(2))(3)N CATALYSTS [J].
TANG, JS ;
MOHAN, T ;
VERKADE, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4931-4938
[29]   A concise route to triazolobenzodiazepine derivatives via a one-pot alkyne-azide cycloaddition reaction [J].
Thomas, AW .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (14) :1881-1884
[30]   Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters [J].
Tripathi, S ;
Misra, K ;
Sanghvi, YS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (22) :5045-5048