Synthesis of 7-alkoxy/hydroxy-α-methyltryptamines

被引：6

作者：

Dubash, NP ^{[1
]}

Mangu, NK ^{[1
]}

Satyam, A ^{[1
]}

机构：

[1] Glenmark Pharmaceut Ltd, Glenmark Res Ctr, Discovery Chem Div, Navi Mumbai, India

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 10期

关键词：

7-methoxy-alpha-methyltryptamine; 7-hydroxy-alpha-methyltryptamine; 7-benzyioxy-alpha-methyltryptamine; Japp-Klingemann coupling; reductive amination;

D O I：

10.1081/SCC-120034160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple method for the preparation of 7-alkoxy/hydroxy-alpha-methyl-DL-tryptamines is reported. The key steps of the synthesis are the Japp-Klingemann coupling of 2-pipetidone-3-carboxylic acid 3 with diazonium salts 4, the Fischer-type cyclization of hydrazones 5 to beta-carboline derivatives 6 and their hydrolysis to title compounds 8.

引用

页码：1791 / 1799

页数：9

共 11 条

[1] TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS .2. A CONVENIENT SYNTHESIS OF TRYPTAMINES AND BETA-CARBOLINES [J].

ABRAMOVITCH, RA ;

SHAPIRO, D .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4589-4592

[2]

[Anonymous], [No title captured], Patent No. 3976639

[3]

Batcho A., 1990, ORG SYNTH, V7, P34

[4]

KATO S, 1998, Patent No. 5817689

[5]

KRUSE LI, 1981, HETEROCYCLES, V16, P1119

[6] NICKEL BORIDE HYDRAZINE HYDRATE - REDUCTION OF AROMATIC AND ALIPHATIC NITROCOMPOUNDS - SYNTHESIS OF 4-(BENZYLOXY)INDOLE AND ALPHA-ALKYLTRYPTAMINES [J].

LLOYD, DH ;

NICHOLS, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4294-4295

[7] SYNTHESIS OF S(+) AND R(-)-3(2-AMINOPROPYL)INDOLE FROM ETHYL-D-L AND L-TRYPTOPHANATE [J].

REPKE, DB ;

FERGUSON, WJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (04) :775-778

[8] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .65. PREPARATION OF 7-METHOXYTRYPTAMINE [J].

SOTI, F ;

INCZE, M ;

KARDOSBALOGH, Z ;

KAJTARPEREDY, M ;

SZANTAY, C .

SYNTHETIC COMMUNICATIONS, 1993, 23 (12) :1689-1698

[9] CONDENSATION OF DIETHYL MALONATE WITH METHYL VINYL KETONE [J].

SPENCER, TA ;

NEWTON, MD ;

BALDWIN, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (04) :787-&

[10]

VANE RB, 1966, Patent No. 3282959

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