Ring expansions of 1-azabicyclo[n.1.0]alkanes. Recent developments

被引:6
作者
Tymoshenko, Dmytro O. [1 ]
机构
[1] AMRI, 26 Corp Circle, Albany, NY 12203 USA
关键词
1-Azabicyclo[n.1.0]alkanes; ring expansion; aziridine; aziridinium; DIELS-ALDER REACTIONS; SUBSTITUTED; 3-FLUOROPIPERIDINES; ASYMMETRIC-SYNTHESIS; CONVENIENT ACCESS; RECEPTOR-BINDING; PIPERIDINES; GENERATION; PYRROLIDINES; DERIVATIVES; 2H-AZIRINES;
D O I
10.3998/ark.5550190.0012.105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the past decade ring expansion of aziridines and aziridiniums fused to other rings has developed into an attractive alternative method to classical pyrrolidine, piperidine and azepine ring construction approaches. This short review provides an update on recent reports and demonstrates the usefulness and the efficiency of this approach.
引用
收藏
页码:329 / 345
页数:17
相关论文
共 57 条
[1]   Formation of pyridin-4(1H)-one versus 1H-azepin-4(7H)-one by treatment of 4-tert-butyldimethylsilyloxy-2-amino-1-azabicyclo[4.1.0]hept-3-enes with tetrabutylammonium fluoride [J].
Alves, M. Jose ;
Fortes, A. Gil ;
Costa, F. Teixeira ;
Duarte, Vera C. M. .
TETRAHEDRON, 2007, 63 (45) :11167-11173
[2]   Generation and Diels-Alder reactions of t-butyl 2H-azirine-3-carboxylate [J].
Alves, MJ ;
Gilchrist, TL .
TETRAHEDRON LETTERS, 1998, 39 (41) :7579-7582
[3]   Synthesis and receptor binding studies of 3-substituted piperazine derivatives [J].
Bedürftig, S ;
Wünsch, B .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (03) :387-396
[4]   A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone [J].
Brandi, A ;
Cicchi, S ;
Paschetta, V ;
Pardo, DG ;
Cossy, J .
TETRAHEDRON LETTERS, 2002, 43 (51) :9357-9359
[5]  
Bremner JB, 2005, PROG HET CH, V17, P389, DOI 10.1016/S0959-6380(05)80338-1
[6]  
Bremner JB, 2004, PROG HET CH, V16, P431
[7]  
Brown D, 2002, J CHEM SOC P1, V1, P2014
[8]   Nucleophilic opening of the aziridine ring in 1-alkyl-1-azoniatricyclo[2.2.1.026]heptanes [J].
Bulanov, MN ;
Sosonyuk, SE ;
Zyk, NV ;
Zefirov, NS .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (03) :415-421
[9]   Azacineole (1,3,3-trimethyl-2-azabicyclo[2.2.2]octane) [J].
Carman, RM ;
Derbyshire, RPC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (04) :319-322
[10]  
Companyó X, 2009, TARG HETEROCYCL SYST, V13, P147