Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines

被引:20
作者
Sun, Hongnan [1 ]
Huang, Binbin [1 ]
Lin, Run [1 ]
Yang, Chao [1 ]
Xia, Wujiong [1 ]
机构
[1] Harbin Inst Technol, Acad Fundamental & Interdisciplinary Sci, State Key Lab Urban Water Resource & Environm, Harbin 150080, Peoples R China
关键词
ammonium persulfate; aziridine; metal free; morpholine; NOREPINEPHRINE REUPTAKE INHIBITOR; SUBSTITUTED AZIRIDINES; DERIVATIVES; REBOXETINE; ALCOHOLS; ROUTE; SALTS; ACID;
D O I
10.3762/bjoc.11.59
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The metal-free synthesis of 2-substituted and 2,3-disubstituted morpholines through a one-pot strategy is described. A simple and inexpensive ammonium persulfate salt enables the reaction of aziridines with halogenated alcohols to proceed via an S(N)2-type ring opening followed by cyclization of the resulting haloalkoxy amine.
引用
收藏
页码:524 / 529
页数:6
相关论文
共 34 条
[1]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[2]   Facile route to 3,5-disubstituted morpholines: Enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines [J].
Dave, R ;
Sasaki, NA .
ORGANIC LETTERS, 2004, 6 (01) :15-18
[3]  
Fokin V.V., 2006, AZIRIDINES EPOXIDES, P443, DOI DOI 10.1002/3527607862.CH12
[4]   Radical cations of phenyl-substituted aziridines:: what are the conditions for ring opening? [J].
Gaebert, C ;
Mattay, J ;
Toubartz, M ;
Steenken, S ;
Müller, B ;
Bally, T .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (04) :1294-1304
[5]   Enantioselective Syntheses of Morpholines and Their Homologues via SN2-Type Ring Opening of Aziridines and Azetidines with Haloalcohols [J].
Ghorai, Manas K. ;
Shukla, Dipti ;
Das, Kalpataru .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) :7013-7022
[6]  
Hajós M, 2004, CNS DRUG REV, V10, P23
[7]   Nucleophilic ring opening of aziridines [J].
Hu, XE .
TETRAHEDRON, 2004, 60 (12) :2701-2743
[8]   SYNTHESIS OF OPTICALLY-ACTIVE 3-MORPHOLINECARBOXYLIC ACID AND TETRAHYDRO-2H-1,4-THIAZINE-3-CARBOXYLIC ACID [J].
KOGAMI, Y ;
OKAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (08) :2963-2965
[9]   A NEW SYNTHESIS OF AZIRIDINIUM SALTS - 2,2-PENTAMETHYLENE-1,1-TETRAMETHYLENEAZIRIDINIUM PERCHLORATE, A PROTOTYPE [J].
LEONARD, NJ ;
JANN, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (24) :6418-6419
[10]   SMALL CHARGED RINGS .2. SYNTHESIS OF AZIRIDINIUM SALTS [J].
LEONARD, NJ ;
JANN, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (24) :4806-&