STEREOSELECTIVE REDUCTION OF SOME INDOLES WITH TRIETHYLSILANE-TRIFLUOROACETIC ACID

被引：70

作者：

LANZILOTTI, AE ^{[1
]}

LITTELL, R ^{[1
]}

FANSHAWE, WJ ^{[1
]}

MCKENZIE, TC ^{[1
]}

LOVELL, FM ^{[1
]}

机构：

[1] AMER CYANAMID CO,LEDERLE LABS,DIV MED RES,PEARL RIVER,NY 10965

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The completely stereoselective reduction of indoles to cis-indolines by triethylsilane-trifluoroacetic acid is demonstrated. A rationalization of this stereoselectivity is offered. The precursor indoles were prepared by the Fisher indole condensation with levulinic acid (7). 3, 4-Dimethoxyhydrazine (6a) gave only the 5, 6-dimethoxyindole 8a while 3, 4-dichlorohydrazine (6d) gave a 1:1 mixture of the isomeric chloroindoles 8d and 8e which were separated by preparative liquid chromatography. © 1979, American Chemical Society. All rights reserved.

引用

页码：4809 / 4813

页数：5

共 31 条

[21] REDUCTION OF INDOLES AND RELATED COMPOUNDS [J].

ROBINSON, B .

CHEMICAL REVIEWS, 1969, 69 (06) :785-+

[22]

RYLANDER PN, 1967, CATALYTIC HYDROGENAT, P373

[23]

SHEN TY, 1966, Patent No. 3316260

[24] CATALYTIC HYDROGENATION OF INDOLES [J].

SMITH, A ;

UTLEY, JHP .

CHEMICAL COMMUNICATIONS, 1965, (18) :427-&

[25] CONFIGURATIONAL ISOMERS OF 3-SUBSTITUTED CIS-HEXAHYDROCARBAZOLES [J].

SMITH, A ;

UTLEY, JHP .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (01) :1-&

[26] PREPARATION OF SOME SUBSTITUTED 2-METHYL-3-INDOLEACETIC ACIDS [J].

STEVENS, FJ ;

HIGGINBOTHAM, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (08) :2206-2207

[27] DERIVATIVES OF HETEROAUXIN .2. SOME SUBSTITUTED 2-METHYL-3-INDOLEACETIC ACIDS [J].

STEVENS, FJ ;

ASHBY, EC ;

DOWNEY, WE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (07) :1680-1682

[28]

WYNNEWOOD IS, 1966, Patent No. 3294805

[29]

1965, Patent No. 3188313

[30]

1968, Patent No. 1551082

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