A new and efficient one-pot synthesis of apomorphine and its ring-a halogenated derivatives

被引:18
作者
Csutoras, C [1 ]
Berenyi, S [1 ]
Makleit, S [1 ]
机构
[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY
关键词
D O I
10.1080/00397919608004535
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rearrangement and O-demethylation of codeine (2) and various 6-demethoxythebaine derivatives 6-11 with morphinane skeletone into apomorphine (3) and its halogenated derivatives 20-24 could, be efficiently executed in a one-pot operation, by treatment with methanesulfonic acid/methionine.
引用
收藏
页码:2251 / 2256
页数:6
相关论文
共 13 条
[1]   O-DEMETHYLATION OF OPIOID DERIVATIVES WITH METHANE SULFONIC-ACID METHIONINE - APPLICATION TO THE SYNTHESIS OF NALOXONE AND ANALOGS [J].
ANDRE, JD ;
DORMOY, JR ;
HEYMES, A .
SYNTHETIC COMMUNICATIONS, 1992, 22 (16) :2313-2327
[2]   EMETIC ACTIVITY OF N-SUBSTITUTED NORAPOMORPHINES [J].
ATKINSON, ER ;
BULLOCK, FJ ;
GRANCHELLI, FE ;
ARCHER, S ;
ROSENBERG, FJ ;
TEIGER, DG ;
NACHOD, FC .
JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (10) :1000-1003
[3]  
BERENYI S, 1984, ACTA CHIM HUNG, V117, P307
[4]  
BERENYI S, 1980, ACTA CHIM HUNG, V103, P365
[5]   A NEW EFFICIENT METHOD FOR THE PREPARATION OF 2-FLUORO-N-PROPYLNORAPOMORPHINE [J].
BERENYI, S ;
HOSZTAFI, S ;
MAKLEIT, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (20) :2693-2694
[6]  
BERENYI S, 1985, ACTA CHIM HUNG, V120, P201
[7]   MORPHINE ALKALOIDS .121. REARRANGEMENT OF MORPHINANDIENES IN METHANESULFONIC-ACID [J].
BERENYI, S ;
CZIRJAK, M ;
MAKLEIT, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (17) :2137-2139
[8]   REGIOSELECTIVE O-DEMETHYLATION OF APORPHINES WITH METHANESULFONIC-ACID METHIONINE - AN EFFICIENT ONE-POT TRANSFORMATION OF THEBAINE TO (R)(-)-2-METHOXYAPOMORPHINE [J].
BERENYI, S ;
CSUTORAS, C ;
GYULAI, S ;
MAKLEIT, S .
SYNTHETIC COMMUNICATIONS, 1995, 25 (03) :283-288
[9]   SYNTHESIS OF SULFUR-CONTAINING MORPHINANE DIENES [J].
BERENYI, S ;
SEPSI, A ;
GYULAI, S ;
SZILAGYI, L .
SYNTHETIC COMMUNICATIONS, 1995, 25 (21) :3307-3314
[10]   APORPHINES .27. MECHANISTIC ASPECTS OF THE REARRANGEMENT OF THEBAINE AND CODEINE ANALOGS IN METHANESULFONIC-ACID - IMPROVED METHOD FOR SYNTHESIS OF N-ALKYLATED APORPHINES [J].
GRANCHELLI, FE ;
FILER, CN ;
SOLOWAY, AH ;
NEUMEYER, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12) :2275-2278