O-DEMETHYLATION OF OPIOID DERIVATIVES WITH METHANE SULFONIC-ACID METHIONINE - APPLICATION TO THE SYNTHESIS OF NALOXONE AND ANALOGS

被引：17

作者：

ANDRE, JD

DORMOY, JR

HEYMES, A

机构：

[1] Sanofi-Chimie, Sisteron, cedex, Route de Gap

来源：

SYNTHETIC COMMUNICATIONS | 1992年 / 22卷 / 16期

关键词：

D O I：

10.1080/00397919208019086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Naloxone 2 was obtained by demethylation of N-allylnoroxycodone 1 with methane sulfonic acid/methionine. This reagent is an excellent substitute for boron tribromide. It was used for the synthesis of analogous derivatives with variable results.

引用

页码：2313 / 2327

页数：15

共 30 条

[1]

ANDRE JD, 1990, Patent No. 359647

[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]

BADET B, 1979, TETRAHEDRON LETT, P1101

[4] NOVEL ANALGESICS AND MOLECULAR REARRANGEMENTS IN MORPHINE-THEBAINE GROUP .3. ALCOHOLS OF 6,14-ENDO-ETHENOTETRAHYDROORIPAVINE SERIES AND DERIVED ANALOGS OF N-ALLYLNORMORPHINE AND -NORCODEINE [J].

BENTLEY, KW ;

HARDY, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3281-&

[5] CLEAVAGE OF ETHERS [J].

BHATT, MV ;

KULKARNI, SU .

SYNTHESIS-STUTTGART, 1983, (04) :249-282

[6] THE CLEAVAGE OF ETHERS [J].

BURWELL, RL .

CHEMICAL REVIEWS, 1954, 54 (04) :615-685

[7]

Casy A. F., 1986, OPIOID ANALGESICS CH

[8] ANALGESICS .1. SYNTHESIS AND ANALGESIC PROPERTIES OF N-SEC-ALKYL-ANDN-TERT-ALKYLNORMORPHINES [J].

DEGRAW, JI ;

LAWSON, JA ;

CRASE, JL ;

JOHNSON, HL ;

ELLIS, M ;

UYENO, ET ;

LOEW, GH ;

BERKOWITZ, DS .

JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (05) :415-422

[9] REGIOSELECTIVE CLEAVAGE OF AROMATIC METHYL ETHERS BY METHANESULPHONIC ACID IN PRESENCE OF METHIONINE [J].

FUJII, N ;

IRIE, H ;

YAJIMA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (20) :2288-2289

[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

← 1 2 3 →