PREPARATION AND REACTIONS OF 1-(TERT-BUTYLDIMETHYLSILYL)-3-LITHIOINDOLE, REGIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED INDOLES

被引：60

作者：

AMAT, M ^{[1
]}

HADIDA, S ^{[1
]}

SATHYANARAYANA, S ^{[1
]}

BOSCH, J ^{[1
]}

机构：

[1] UNIV BARCELONA,FAC PHARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 01期

关键词：

D O I：

10.1021/jo00080a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-(tert-Butyldimethylsilyl)-3-lithioindole (2) is prepared by metalation of the corresponding 3-bromo derivative 1 and efficiently reacts with electrophiles to give 3-substituted indoles 3 and 4. © 1994, American Chemical Society. All rights reserved.

引用

页码：10 / 11

页数：2

共 43 条

[1] AN EFFICIENT SYNTHESIS OF 2-(2-PYRIDYL)INDOLES BY PALLADIUM(0)-CATALYZED HETEROARYLATION [J].

AMAT, M ;

HADIDA, S ;

BOSCH, J .

TETRAHEDRON LETTERS, 1993, 34 (31) :5005-5006

[2] CYCLOHEXADIENONE ANNULATIONS OF ARYL CARBENE COMPLEXES OF CHROMIUM - NEW STRATEGIES FOR THE SYNTHESIS OF INDOLE ALKALOIDS [J].

BAUTA, WE ;

WULFF, WD ;

PAVKOVIC, SF ;

ZALUZEC, EJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3249-3252

[3] TOTAL SYNTHESIS OF YUEHCHUKENE [J].

BERGMAN, J ;

VENEMALM, L .

TETRAHEDRON LETTERS, 1988, 29 (24) :2993-2994

[4] NOVEL SYNTHESIS OF INDOLE ALKALOID ELLIPTICINE [J].

BESSELIEVRE, R ;

THAL, C ;

HUSSON, HP ;

POTIER, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (03) :90-91

[5] THE SYNTHESIS OF 4-SUBSTITUTED INDOLES VIA ARENETRICARBONYLCHROMIUM(O) COMPLEXES [J].

BESWICK, PJ ;

GREENWOOD, CS ;

MOWLEM, TJ ;

NECHVATAL, G ;

WIDDOWSON, DA .

TETRAHEDRON, 1988, 44 (23) :7325-7334

[6]

BRAY BL, 1990, J ORG CHEM, V55, P6137

[7]

BUTTERY CD, 1991, SYNLETT, P315

[8] N-METHYL LITHIATION OF N-METHYLINDOLES DIRECTED BY ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

KILLPACK, MO .

TETRAHEDRON LETTERS, 1989, 30 (33) :4337-4340

[9] LITHIATION OF HETEROCYCLES DIRECTED BY ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

KILLPACK, MO .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :104-109

[10]

CONWAY SC, 1990, HETEROCYCLES, V30, P627

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