PREPARATION OF 2,3-DISUBSTITUTED INDOLES FROM INDOLE-3-CARBOXYLIC ACIDS AND AMIDES BY ALPHA-DEPROTONATION

被引：11

作者：

BUTTERY, CD ^{[1
]}

JONES, RG ^{[1
]}

KNIGHT, DW ^{[1
]}

机构：

[1] DEPT CHEM,UNIV PK,NOTTINGHAM NG7 2RD,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 13期

关键词：

D O I：

10.1039/p19930001425

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct deprotonations have been used to obtain the 2(alpha)-lithiated indole-3-carboxylate dianions 8 and 14, together with the related 2(alpha)-lithiated indole-3-carboxamide monoanions 18 and 20b from the parent compounds. These four intermediates are useful for the preparation of 2,3-disubstituted indoles, especially by condensations with aldehydes and ketones and by alkylations using primary alkyl iodides.

引用

页码：1425 / 1431

页数：7

共 32 条

[1] STUDIES ON THE SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS - A DIRECT ENTRY TO 4-ETHYLIDENE-HEXAHYDRO-1,5-METHANOAZOCINO[4,3-B]INDOLES
ALVAREZ, M
LAVILLA, R
BOSCH, J
[J]. TETRAHEDRON LETTERS, 1987, 28 (38) : 4457 - 4460
[2] REACTION OF INDOLE AND INDOLE GRIGNARD-REAGENT WITH PHOSGENE - FACILE SYNTHESIS OF INDOLE-3-CARBOXYLIC ACID-DERIVATIVES
BERGMAN, J
CARLSSON, R
SJOBERG, B
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (07) : 1123 - 1134
[3] BUTTERY CD, 1991, SYNLETT, P315
[4] THE GENERATION AND SYNTHETIC UTILITY OF DIANIONS DERIVED FROM BENZOFURANCARBOXYLIC ACIDS
BUTTERY, CD
KNIGHT, DW
NOTT, AP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12): : 2839 - 2843
[5] HIGH-YIELD SYNTHESES OF 2,3-DISUBSTITUTED FURANS AND THIOPHENES
CARPENTER, AJ
CHADWICK, DJ
[J]. TETRAHEDRON LETTERS, 1985, 26 (14) : 1777 - 1780
[6] LITHIATION OF HETEROCYCLES DIRECTED BY ALPHA-AMINO ALKOXIDES
COMINS, DL
KILLPACK, MO
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) : 104 - 109
[7] CONWAY SC, 1992, HETEROCYCLES, V34, P2095
[8] REGIOSELECTIVITY IN THE LITHIATION OF METHYL-SUBSTITUTED THIAZOLE-CARBOXYLIC AND OXAZOLE-CARBOXYLIC ACIDS AND CARBOXAMIDES - GENERAL-METHODS FOR THE ELABORATION OF TRISUBSTITUTED THIAZOLES AND OXAZOLES
CORNWALL, P
DELL, CP
KNIGHT, DW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10): : 2417 - 2428
[9] DIANIONS OF METHYLATED THIOPHENE-2-CARBOXYLIC ACIDS - THEIR FORMATION AND REACTIVITY
GOULD, NP
LEE, TJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) : 4528 - 4530
[10] SYNTHESIS AND DIELS-ALDER REACTIONS OF 1,3-DIMETHYL-4-(PHENYLSULFONYL)-4H-FURO[3,4-B]INDOLE - A NEW ANNULATION STRATEGY FOR THE CONSTRUCTION OF ELLIPTICINE AND ISOELLIPTICINE
GRIBBLE, GW
SAULNIER, MG
SIBI, MP
OBAZANUTAITIS, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) : 4518 - 4523

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