Synthesis of 2-azabicyclo[3.3.1]nonanes by means of (carbamoyl)dichloromethyl radical cyclization

被引:53
作者
Quirante, J [1 ]
Escolano, C [1 ]
Massot, M [1 ]
Bonjoch, J [1 ]
机构
[1] UNIV BARCELONA,FAC FARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1016/S0040-4020(96)01051-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new procedure for the synthesis of 2-azabicyclo[3.3.1]nonanes by intramolecular carboradical cyclization of 4-(trichloroacetamido)cyclohexenes substituted with an electron withdrawing substituent (ester or nitrile) is described. The procedure allows the preparation of synthetically interesting azabicyclos 14 and 15 in nearly 70% yield. (C) 1997, Elsevier Science Ltd.
引用
收藏
页码:1391 / 1402
页数:12
相关论文
共 65 条
[1]   REVERSAL OF STEREOSELECTIVITY IN THE REDUCTION OF GEM-DICHLORIDES BY TRIBUTYLTIN HYDRIDE AND TRIS(TRIMETHYLSILYL)SILANE - SYNTHETIC AND MECHANISTIC IMPLICATIONS [J].
APELOIG, Y ;
NAKASH, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10781-10782
[2]   THE SYNTHESIS OF INDOLIZIDINE AND QUINOLIZIDINE RING-SYSTEMS BY FREE-RADICAL CYCLIZATION OF 4-AZA-6-METHOXYCARBONYL-5-HEXENYL RADICALS [J].
BECKWITH, ALJ ;
WESTWOOD, SW .
TETRAHEDRON, 1989, 45 (16) :5269-5282
[3]   SYNTHETIC ANALGESICS - PREPARATION OF RACEMIC 6,7-BENZOMORPHANS [J].
BOGER, DL ;
PATEL, M ;
MULLICAN, MD .
TETRAHEDRON LETTERS, 1982, 23 (44) :4559-4562
[4]   STUDIES ON THE SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS - SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE [J].
BONJOCH, J ;
SOLE, D ;
BOSCH, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11017-11018
[5]   SYNTHESIS OF 2-AZABICYCLO[3.3.1]NONANES [J].
BOSCH, J ;
BONJOCH, J .
HETEROCYCLES, 1980, 14 (04) :505-529
[6]  
BOYER FD, 1992, SYNLETT, P357
[7]  
BRUMWELL JE, 1994, TETRAHEDRON, V50, P13533
[8]   HEXENYL RADICAL CYCLIZATION VIA PHENYL SELENIDE TRANSFER [J].
BYERS, JH ;
GLEASON, TG ;
KNIGHT, KS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) :354-356
[9]   PALLADIUM-CATALYZED CARBONYLATION OF ENOL TRIFLATES - A NOVEL METHOD FOR ONE-CARBON HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES [J].
CACCHI, S ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1985, 26 (08) :1109-1112
[10]   FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .15. C-13 NMR CHEMICAL-SHIFT ASSIGNMENTS FOR SUBSTITUTED 2-AZABICYCLO[3.3.1] NONAN-7-ONES [J].
CASAMITJANA, N ;
BONJOCH, J ;
GRACIA, J ;
BOSCH, J .
MAGNETIC RESONANCE IN CHEMISTRY, 1992, 30 (02) :183-185