Unconventional Passerini Reaction toward α-Aminoxy-amides

被引:30
作者
Chandgude, Ajay L. [1 ]
Domling, Alexander [1 ]
机构
[1] Univ Groningen, Dept Drug Design, Antonius Deusinglaan 1, NL-9713 AV Groningen, Netherlands
关键词
MULTICOMPONENT REACTIONS; NORSTATINE ANALOGS; CYCLIC HEXAPEPTIDE; CHLORIDE-ION; ACIDS; PEPTIDES; PEPTIDOMIMETICS; FOLDAMERS; ISOCYANIDES; CHEMISTRY;
D O I
10.1021/acs.orglett.6b03293
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Passerini multicomponent reaction (P-3CR) toward the one-step synthesis of alpha-aminoxy-amide, by employing for the first time a N-hydroxamic acid component, has been reported. The sonication-accelerated, catalyst-free, simple, fast, and highly efficient Passerini reaction is used for the synthesis of diverse alpha-aminoxy-amides. The reaction is compatible with a vast range of aldehydes, isocyanides, and N-hydroxamic acids such as N-hydroxysuccinimides and phthalimides. The generated Passerini products can be easily converted into several follow-up products.
引用
收藏
页码:6396 / 6399
页数:4
相关论文
共 44 条
[1]   The Joint European Compound Library: boosting precompetitive research [J].
Besnard, Jeremy ;
Jones, Philip S. ;
Hopkins, Andrew L. ;
Pannifer, Andrew D. .
DRUG DISCOVERY TODAY, 2015, 20 (02) :181-186
[2]   An efficient Passerini tetrazole reaction (PT-3CR) [J].
Chandgude, Ajay L. ;
Domling, Alexander .
GREEN CHEMISTRY, 2016, 18 (13) :3718-3721
[3]   Extraordinary metabolic stability of peptides containing α-aminoxy acids [J].
Chen, Fei ;
Ma, Bin ;
Yang, Zong-Chang ;
Lin, Ge ;
Yang, Dan .
AMINO ACIDS, 2012, 43 (01) :499-503
[4]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[5]  
2-U
[6]   Chemistry and Biology Of Multicomponent Reactions [J].
Domling, Alexander ;
Wang, Wei ;
Wang, Kan .
CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135
[7]   Smiles rearrangements in Ugi- and Passerini-type couplings:: New multicomponent access to O- and N-arylamides [J].
El Kaim, Laurent ;
Gizolme, Marie ;
Grimaud, Laurence ;
Oble, Julie .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (11) :4169-4180
[8]   O-arylative Passerini reactions [J].
El Kaim, Laurent ;
Gizolme, Marie ;
Grimaud, Laurence .
ORGANIC LETTERS, 2006, 8 (22) :5021-5023
[9]   PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES [J].
GIANNIS, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) :1244-1267
[10]   Therapeutic Potential of Foldamers: From Chemical Biology Tools To Drug Candidates? [J].
Gopalakrishnan, Ranganath ;
Frolov, Andrey I. ;
Knerr, Laurent ;
Drury, William J., III ;
Valeur, Eric .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (21) :9599-9621