Non-conventional redox chemistry of dihydropyridines and pyridinium salts

被引:13
作者
Lavilla, R
机构
[1] Univ Barcelona, Organ Chem Lab, Fac Pharm, E-08028 Barcelona, Spain
[2] Parc Cient Barcelona, E-08028 Barcelona, Spain
关键词
D O I
10.2174/1385272043370690
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The classical redox chemistry of the NADH-NAD(+) cofactors and their synthetic analogues (dihydropyridines and pyridinium salts) has been extended to non-biomimetic processes. These involve reactions that bypass the electron transfer processes and alloy the functionalization of the heterocyclic parent systems with a broad variety of carbon-and heteroatom-based functional groups. The scope of the methodology, and its applications to organic synthesis are analyzed.
引用
收藏
页码:715 / 737
页数:23
相关论文
共 99 条
[1]   ELECTRON VERSUS HYDRIDE ION TRANSFER IN THE REDUCTION OF BETA-HALOGEN-SUBSTITUTED 1,2-DIOXETANES BY 1,4-DIHYDRONICOTINAMIDES [J].
ADAM, W ;
HEIL, M ;
HUTTERER, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) :4491-4495
[2]   EPOXIDATION OF VINYLAMIDES BY DIMETHYLDIOXIRANE - FIRST SPECTRAL EVIDENCE FOR ENAMIDE OXIDES [J].
ADAM, W ;
REINHARDT, D ;
REISSIG, HU ;
PAULINI, K .
TETRAHEDRON, 1995, 51 (45) :12257-12262
[3]  
AMANN R, 1991, ANGEW CHEM, V103, P1373
[4]  
[Anonymous], [No title captured]
[5]  
BENNASAR ML, 1988, HETEROCYCLES, V27, P291
[6]   METHOD FOR THE SYNTHESIS OF BRIDGED INDOLE ALKALOIDS - ADDITION OF CARBON NUCLEOPHILES TO N-ALKYLPYRIDINIUM SALTS [J].
BOSCH, J ;
BENNASAR, ML .
SYNLETT, 1995, (06) :587-596
[7]   REACTIVITY OF BIOLOGICALLY IMPORTANT REDUCED PYRIDINES .4. EFFECT OF SUBSTITUTION ON FERRICYANIDE-MEDIATED OXIDATION RATES OF VARIOUS 1,4-DIHYDROPYRIDINES [J].
BREWSTER, ME ;
SIMAY, A ;
CZAKO, K ;
WINWOOD, D ;
FARAG, H ;
BODOR, N .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3721-3726
[8]   Conformational memory in enantioselective radical reductions and a new radical clock reaction [J].
Buckmelter, AJ ;
Kim, AI ;
Rychnovsky, SD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) :9386-9390
[9]   The preparation of alpha-substituted, beta-hydroxy piperidines and pyrrolidines: The total synthesis of Febrifugine. [J].
Burgess, LE ;
Gross, EKM ;
Jurka, J .
TETRAHEDRON LETTERS, 1996, 37 (19) :3255-3258
[10]   On the regio- and stereoselectivity of pyridinyl radical dimerization [J].
Carelli, V ;
Liberatore, F ;
Casini, A ;
Tortorella, S ;
Scipione, L ;
Di Rienzo, B .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (09) :999-1004