THIENOQUINOLIZIDINONES - SYNTHESIS AND REARRANGEMENT INTO NEW PIPERIDINO[1,2-A][1,3] OR [1,4]DIAZEPINONES FUSED TO A THIOPHENE RING

被引:20
作者
MARCHALIN, S [1 ]
DECROIX, B [1 ]
机构
[1] UNIV HAVRE, UER SCI & TECH, LAB CHIM, F-76600 LE HAVRE, FRANCE
关键词
D O I
10.1002/jhet.5570310239
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient route to thienoquinolizidinones is described starting from ethyl pipecolinate and suitable halogenomethylthiophenes or 3-chloromethylbenzothiophene. The Schmidt reaction and the Beckmann rearrangement of oximes of these ketones led to piperidino[1,2-a][1,3] or [1,4] diazepines fused to a thiophene ring.
引用
收藏
页码:495 / 499
页数:5
相关论文
共 14 条
[1]   LUPINEN-ALKALOIDE .8. ZUR KONFIGURATIONSBESTIMMUNG VON CHINOLIZIDIN-DERIVATEN [J].
BOHLMANN, F .
CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (10) :2157-2167
[2]   SYNTHESIS OF PHENANTHROINDOLIZIDINES .2. SYNTHESIS OF (+/-)-TYLOCREBRINE, (+/-)-TYLOPHORINE, (+/-)-ANTOFINE, AND (+/-)-2,3-DI ETHOXYPHENANTHROINDOLIZIDINE [J].
CHAUNCY, B ;
GELLERT, E .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1970, 23 (12) :2503-&
[3]   REARRANGEMENT OF THIENOBENZOTHIEPINONES TO THIENOISOTHIAZOLINONE AND BENZOISOTHIAZOLINONE [J].
DAICH, A ;
DECROIX, B .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (08) :1881-1884
[4]  
DAICH A, 1992, J HETEROCYCLIC CHEM, V28, P1911
[5]  
FERNANDEZ M, 1986, HETEROCYCLES, V24, P1589
[6]   THE C-13 NMR-SPECTRA OF THIOPHENES .2. 2-SUBSTITUTED THIOPHENES [J].
FUJIEDA, K ;
TAKAHASHI, K ;
SONE, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (05) :1587-1588
[7]   SYNTHESIS OF INDOLIZINE-6,9-DIONES ANNELATED TO A THIOPHENE RING [J].
MARCHALIN, S ;
DECROIX, B ;
MOREL, J .
ACTA CHEMICA SCANDINAVICA, 1993, 47 (03) :287-291
[8]   DIAZEPINES AND NAPHTHYRIDINES FROM THE REARRANGEMENT OF THIENOINDOLIZIDINONE OXIMES [J].
MARCHALIN, S ;
DECROIX, B .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (03) :667-670
[9]   CYCLIC LACTAMS . HEXAHYDRODIBENZAZEPINONES FROM 1,2,3,4,4A,9,10,10A-(TRANS-4A,10A)-OCTAHYDRO-9-OXOPHENANTHRENE [J].
NELSON, WL ;
MILLER, DD ;
WILSON, RS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (01) :131-&
[10]   THE SCHMIDT REACTION - EXPERIMENTAL CONDITIONS AND MECHANISM [J].
SMITH, PAS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (01) :320-323