FACILE ACCESS TO 3-ALKYL-SUBSTITUTED 3-HYDROPEROXY-2,4-PYRROLIDINEDIONES USING MANGANESE(III)-CATALYZED AEROBIC OXIDATION

被引:13
作者
Haque, M. Aminul [1 ]
Nishino, Hiroshi [1 ]
机构
[1] Kumamoto Univ, Dept Chem, Grad Sch Sci & Technol, Kumamoto 8608555, Japan
基金
日本学术振兴会;
关键词
Aerobic oxidation; catalytic oxidation; hydroperoxidation; hydroperoxypyrrolidinediones; manganese(III) acetate; 2,4-pyrrolidinediones; DERIVATIVES; ARTEMISININ; PHENYLBUTAZONE; PEROXIDES;
D O I
10.1080/00397911.2010.528129
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Alkyl-substituted 2,4-pyrrolidinediones were directly oxidized under very mild manganese(III)-catalyzed aerobic oxidation conditions to give the corresponding 3-hydroperoxy-2,4-pyrrolidinediones in quantitative yields. The scope and limitations for the synthesis of the hydroperoxyprrolidinediones are described.
引用
收藏
页码:608 / 619
页数:12
相关论文
共 33 条
[1]   CONCISE SYNTHESIS OF YINGZHAOSU-C AND EPI-YINGZHAOSU-C BY PEROXYL RADICAL CYCLIZATION - ASSIGNMENT OF RELATIVE CONFIGURATION [J].
BOUKOUVALAS, J ;
POULIOT, R ;
FRECHETTE, Y .
TETRAHEDRON LETTERS, 1995, 36 (24) :4167-4170
[2]   ACTIVATED CYCLOPHOSPHAMIDE ANTI-CANCER DRUGS - MOLECULAR-STRUCTURES OF CIS-4-HYDROPEROXYISOPHOSPHAMIDES AND TRANS-4-HYDROPEROXYISOPHOSPHAMIDES [J].
CAMERMAN, A ;
SMITH, HW ;
CAMERMAN, N .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (05) :679-683
[3]   STRUCTURES OF 2 ISOMERIC BICYCLIC DERIVATIVES OF 4-HYDROPEROXYISOPHOSPHAMIDE [J].
CAMERMAN, N ;
FAWCETT, JK ;
CAMERMAN, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (05) :683-686
[4]  
Casteel DA, 1999, NAT PROD REP, V16, P55
[5]  
Chowdhury FA, 1999, HETEROCYCLES, V51, P575
[6]  
COYNE WE, 1970, MED CHEM, P953
[7]   Bioactive peroxides as potential therapeutic agents [J].
Dembitsky, Valery M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (02) :223-251
[8]   THE PREPARATION OF SUBSTITUTED HYDRAZINES .1. ALKYLHYDRAZINES VIA ALKYLSYDNONES [J].
FUGGER, J ;
TIEN, JM ;
HUNSBERGER, IM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (07) :1843-1848
[9]   Antimalarial Peroxide Dyads from Natural Artemisinin and Hydroxyalkylated 1,2,4-Trioxanes [J].
Griesbeck, Axel G. ;
Neudoerfl, Joerg ;
Hoerauf, Achim ;
Specht, Sabine ;
Raabe, Angela .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (10) :3420-3423
[10]  
Halliwell B., 1989, Free radicals in biology and medicine, V2nd, P1