A two-step method for the preparation of homochiral cathinones

被引：23

作者：

Osorio-Olivares, M

Rezende, MC

Sepúlveda-Boza, S

Cassels, BK

Baggio, RF

Muñoz-Acevedo, JC

机构：

[1] Univ Santiago Chile, Fac Quim & Biol, Santiago, Chile

[2] Univ Santiago Chile, Fac Ciencias Med, Santiago, Chile

[3] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

[4] Univ Chile, Fac Ciencias, Millennium Inst Adv Studies Cell Biol & Biotechno, Santiago, Chile

[5] Comis Nacl Energia Atom, Dept Fis, RA-1429 Buenos Aires, DF, Argentina

[6] Univ Chile, Fac Ciencias Fis & Matemat, Santiago, Chile

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(03)00317-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple method for the preparation of homochiral ring-substituted 1-aryl-2-aminopropanones 2 ('cathinones') is described, involving initial Friedel-Crafts acylation of aromatics with (S)- or (R)-N-trifluoroacetylalanyl chloride, followed by acid hydrolysis of the intermediate trifluoroacetamido intermediates 1. for which X-ray diffraction analysis confirmed the structures. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：1473 / 1477

页数：5

相关论文

共 18 条

[1] ENANTIOMERIC ALPHA-AMINOPROPIOPHENONES (CATHINONE) - PREPARATION AND INVESTIGATION [J].

BERRANG, BD ;

LEWIN, AH ;

CARROLL, FI .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2643-2647

[2] Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT2A/2C receptor agonists [J].

Chambers, JJ ;

Kurrasch-Orbaugh, DM ;

Parker, MA ;

Nichols, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :1003-1010

[3] Comparison of analgesic effects of khat (Catha edulis Forsk) extract, D-amphetamine and ibuprofen in mice [J].

Connor, J ;

Makonnen, E ;

Rostom, A .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 2000, 52 (01) :107-110

[4] Comparison of effects of khat extract and amphetamine on motor behaviors in mice [J].

Connor, JD ;

Rostom, A ;

Makonnen, E .

JOURNAL OF ETHNOPHARMACOLOGY, 2002, 81 (01) :65-71

[5] TRIFLUOROACETYLATION OF AMINO-ACIDS AND PEPTIDES BY ETHYL TRIFLUOROACETATE [J].

CURPHEY, TJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2805-2807

[6] Cathinone: An investigation of several N-alkyl and methylenedioxy-substituted analogs [J].

DalCason, TA ;

Young, R ;

Glennon, RA .

PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1997, 58 (04) :1109-1116

[7]

HUANG X, 1992, EUR J PHARMACOL, V229, P3

[8] FRIEDEL-CRAFTS ALPHA-AMINOACYLATION OF ALKYLBENZENE WITH A CHIRAL N-CARBOXY-ALPHA-AMINO ACID ANHYDRIDE WITHOUT LOSS OF CHIRALITY [J].

ITOH, O ;

HONNAMI, T ;

AMANO, A ;

MURATA, K ;

KOICHI, Y ;

SUGITA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7334-7338

[9] FRIEDEL-CRAFTS ACYLATION WITH N-(TRIFLUOROACETYL)-ALPHA-AMINO ACID-CHLORIDES - APPLICATION TO THE PREPARATION OF BETA-ARYLALKYLAMINES AND 3-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES [J].

NORDLANDER, JE ;

PAYNE, MJ ;

NJOROGE, FG ;

BALK, MA ;

LAIKOS, GD ;

VISHWANATH, VM .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4107-4111

[10] N-(TRIFLUOROACETYL)-ALPHA-AMINO ACID-CHLORIDES AS CHIRAL REAGENTS FOR FRIEDEL-CRAFTS SYNTHESIS [J].

NORDLANDER, JE ;

NJOROGE, FG ;

PAYNE, MJ ;

WARMAN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3481-3484