Ortho-directed metalation of 3-carboxy-β-carbolines:: Use of the SmI2-cleavable 9-N-(N′,N′-dimethylsulfamoyl) blocking group for the preparation of 9-N-deprotected 4-amino derivatives via azide introduction or a palladium-catalyzed cross-coupling reaction

被引：50

作者：

Batch, A ^{[1
]}

Dodd, RH ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 03期

关键词：

D O I：

10.1021/jo971485l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[No abstract available]

引用

页码：872 / 877

页数：6

共 30 条

[1] PREPARATION AND REACTIONS OF 1-(TERT-BUTYLDIMETHYLSILYL)-3-LITHIOINDOLE, REGIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED INDOLES
AMAT, M
HADIDA, S
SATHYANARAYANA, S
BOSCH, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) : 10 - 11
[2] URINARY AND BRAIN BETA-CARBOLINE-3-CARBOXYLATES AS POTENT INHIBITORS OF BRAIN BENZODIAZEPINE RECEPTORS
BRAESTRUP, C
NIELSEN, M
OLSEN, CE
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (04): : 2288 - 2292
[3] BETA-CARBOLINES - SYNTHESIS AND NEUROCHEMICAL AND PHARMACOLOGICAL ACTIONS ON BRAIN BENZODIAZEPINE RECEPTORS
CAIN, M
WEBER, RW
GUZMAN, F
COOK, JM
BARKER, SA
RICE, KC
CRAWLEY, JN
PAUL, SM
SKOLNICK, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (09) : 1081 - 1091
[4] 2,5-DILITHIATION OF N-PROTECTED IMIDAZOLES - SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES OF 1-METHOXYMETHYL-IMIDAZOLE, 1-TRIPHENYLMETHYL-IMIDAZOLE, AND 1-(N,N-DIMETHYLSULPHONAMIDO)-IMIDAZOLE
CHADWICK, DJ
NGOCHINDO, RI
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03): : 481 - 486
[5] DODD RH, 1992, CAH PSYCHOL COGN, V12, P484
[6] SYNTHETIC ROUTES TO 4-AMINO-3-CARBOXY-BETA-CARBOLINE DERIVATIVES - INCIDENTAL FORMATION OF NOVEL FURO[3,4-C]-BETA-CARBOLIN-2-ONES DISPLAYING HIGH AFFINITIES FOR THE BENZODIAZEPINE RECEPTOR
DOREY, G
DUBOIS, L
DECARVALHO, LP
POTIER, P
DODD, RH
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (01) : 189 - 198
[7] APPLICATION OF ORGANO-LITHIUM AND RELATED REAGENTS IN SYNTHESIS .7. SYNTHESIS AND METALATION OF 4-METHOXYPICOLIN-ANILIDES AND 2-METHOXYISONICOTIN-ANILIDES - A USEFUL METHOD FOR PREPARATION OF 2,3,4-TRISUBSTITUTED PYRIDINES
EPSZTAJN, J
BIENIEK, A
PLOTKA, MW
SUWALD, K
[J]. TETRAHEDRON, 1989, 45 (23) : 7469 - 7476
[8] EPSZTAJN J, 1986, J CHEM RES-S, P20
[9] ELECTROPHILIC AZIDE TRANSFER TO CHIRAL ENOLATES - A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS
EVANS, DA
BRITTON, TC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) : 6881 - 6883
[10] SYNTHESES OF FUNCTIONALIZED PYRIDO[2,3-B]INDOLES
FORBES, IT
JOHNSON, CN
THOMPSON, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02): : 275 - 281

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