Ru/C catalyzed cyclization of linear α,ω-diamines to cyclic amines in water

被引:21
作者
Gadda, Thomas M. [1 ]
Yu, Xiao-Yan [1 ]
Miyazawa, Akira [1 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, NRI, Higashi Ku, Tsukuba, Ibaraki 3058565, Japan
关键词
Cyclic amine; Ru/C; Synthesis; Water; Cyclization; Intramolecular; Ring-closure; Deuteration; SECONDARY-AMINES; CONVENIENT SYNTHESIS; TERTIARY-AMINES; PIPERIDINES; REDUCTION; TRANSFORMATION; RUCL2(PH3P)3; AZIRIDINES; CONVERSION; ALKENES;
D O I
10.1016/j.tet.2009.12.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and convenient way to prepare cyclic amines in water was achieved by the catalyst system composed of Ru/C and Al powder The alpha,omega-diaminoalkanes, 1.4-diaminobutane, 1,5-diaminopentane. and 1.6-diamino-heptane were converted to corresponding cyclic amines in good yields The Use Of D2O provided a novel route to obtain deuterated cyclic amines in good yields (C) 2009 Elsevier Ltd All rights reserved
引用
收藏
页码:1249 / 1253
页数:5
相关论文
共 32 条
[1]   One-step exchange-labelling of piperidines, piperazines and dialkylamines with deuterium oxide: catalysis by various ruthenium complexes [J].
Alexakis, E ;
Hickey, MJ ;
Jones, JR ;
Kingston, LP ;
Lockley, WJS ;
Mather, AN ;
Smith, T ;
Wilkinson, DJ .
TETRAHEDRON LETTERS, 2005, 46 (25) :4291-4293
[2]   SELECTIVE CONVERSION OF PRIMARY AMINES INTO N,N-DIMETHYLALKYL-AMINE OR N,N-DIALKYLMETHYL-AMINE WITH METHANOL AND RUCL2(PH3P)3 [J].
ARCELLI, A ;
BUITHEKHAI ;
PORZI, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 235 (01) :93-96
[3]  
Challis B. C., 1968, CHEM AMINO GROUP, P277
[4]   AMBIDENT NEIGHBORING GROUPS .5. MECHANISM OF CYCLIZATION OF 2-HALOGENOETHYLSULFONAMIDES TO AZIRIDINES [J].
COY, JH ;
HEGARTY, AF ;
FLYNN, EJ ;
SCOTT, FL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (01) :53-58
[5]  
DEANGELIS F, 1979, SYNTHESIS-STUTTGART, P70
[6]   ELECTROPHILE-INDUCED CYCLIZATION OF GAMMA,DELTA-ALKENYLIMINES AS A SYNTHETIC ROUTE TO PYRROLIDINES AND PIPERIDINES [J].
DEKIMPE, N ;
BOELENS, M ;
PIQUEUR, J ;
BAELE, J .
TETRAHEDRON LETTERS, 1994, 35 (12) :1925-1928
[7]  
DEKIMPE N, 1994, TETRAHEDRON LETT, V35, P8023, DOI 10.1016/0040-4039(94)80039-1
[8]   RING-CLOSURE REACTIONS .23. KINETICS OF FORMATION OF 3-MEMBERED-RING N-TOSYLAZACYCLOALKANES TO 7-MEMBERED-RING N-TOSYLAZACYCLOALKANES - THE ROLE OF RING STRAIN IN SMALL-SIZED-RING AND COMMON-SIZED-RING FORMATION [J].
DIMARTINO, A ;
GALLI, C ;
GARGANO, P ;
MANDOLINI, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (09) :1345-1349
[9]   The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions:: a new route to secondary amines [J].
Doctorovich, F ;
Trápani, C .
TETRAHEDRON LETTERS, 1999, 40 (25) :4635-4638
[10]  
Khai