A simple and efficient one step synthesis of benzoxazoles and benzimidazoles from carboxylic acids

被引:155
作者
Wang, Ying [1 ]
Sarris, Kathy [1 ]
Sauer, Daryl R. [1 ]
Djuric, Stevan W. [1 ]
机构
[1] Abbott Labs, Global Pharmaceut Res & Dev, Med Chem Technol, High Throughput Organ Synth Grp, Abbott Pk, IL 60064 USA
关键词
D O I
10.1016/j.tetlet.2006.05.052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzoxazoles or benzimidazoles can be rapidly and efficiently synthesized from a variety of carboxylic acids with 2-aminophenols or 1,2-phenylenediamines in one simple step, respectively. The use of commercially available PS-PPh3 resin combined with microwave heating delivered a variety of benzoxazoles and benzimidazoles in high yields and purities. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4823 / 4826
页数:4
相关论文
共 20 条
[1]   Solid-phase synthesis of benzoxazoles from 3-nitrotyrosine [J].
Beebe, X ;
Wodka, D ;
Sowin, TJ .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (04) :360-366
[2]   Hit and lead generation:: Beyond high-throughput screening [J].
Bleicher, KH ;
Böhm, HJ ;
Müller, K ;
Alanine, AI .
NATURE REVIEWS DRUG DISCOVERY, 2003, 2 (05) :369-378
[3]  
Boyd G. V., 2002, SCI SYNTHESIS, P481
[4]   Efficient procedure for the preparation of amides using polymer-bound reagents [J].
Buchstaller, HP ;
Ebert, HM ;
Anlauf, U .
SYNTHETIC COMMUNICATIONS, 2001, 31 (07) :1001-1005
[5]   Synthesis of benzimidazole based analogues of sphingosine-1-phosphate:: discovery of potent, subtype-selective S1P4 receptor agonists [J].
Clemens, JJ ;
Davis, MD ;
Lynch, KR ;
Macdonald, TL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (19) :4903-4906
[6]   Microbial hydroxylation of 2-cycloalkylbenzoxazoles .2. Determination of product structures and enhancement of enantiomeric excess [J].
deRaadt, A ;
Griengl, H ;
Petsch, M ;
Plachota, P ;
Schoo, N ;
Weber, H ;
Braunegg, G ;
Kopper, I ;
Kreiner, M ;
Zeiser, K .
TETRAHEDRON-ASYMMETRY, 1996, 7 (02) :473-490
[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]  
GRIMMETT MR, 2002, SCI SYNTHESIS, P529
[10]   Molecular complexity and its impact on the probability of finding leads for drug discovery [J].
Hann, MM ;
Leach, AR ;
Harper, G .
JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 2001, 41 (03) :856-864