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
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
收藏
页码:872 / 877
页数:6
相关论文
共 30 条
[21]   ORTHO-DIRECTED LITHIATION STUDIES OF 3-CARBOXY-BETA-CARBOLINES - A DIRECT ROUTE TO 4-SUBSTITUTED DERIVATIVES [J].
MEHTA, A ;
DODD, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7587-7590
[22]  
NEEF G, 1983, HETEROCYCLES, V20, P1295
[23]   STUDY OF THE LITHIATION OF 3-SUBSTITUTED ALPHA-CARBOLINES - A NEW ROUTE TO 3,4-DISUBSTITUTED DERIVATIVES [J].
PAPAMICAEL, C ;
DUPAS, G ;
BOURGUIGNON, J ;
QUEGUINER, G .
TETRAHEDRON LETTERS, 1994, 35 (24) :4099-4102
[24]   DIRECTED METALATION OF PI-DEFICIENT AZAAROMATICS - STRATEGIES OF FUNCTIONALIZATION OF PYRIDINES, QUINOLINES, AND DIAZINES [J].
QUEGUINER, G ;
MARSAIS, F ;
SNIECKUS, V ;
EPSZTAJN, J .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1991, 52 :187-304
[25]  
SCHLECKER W, 1995, SYNTHESIS-STUTTGART, P1225
[26]   BETA-CARBOLINES AS AGONISTIC OR ANTAGONISTIC BENZODIAZEPINE RECEPTOR LIGANDS .1. SYNTHESIS OF SOME 5-AMINO, 6-AMINO AND 7-AMINO DERIVATIVES OF 3-METHOXYCARBONYL-BETA-CARBOLINE (BETA-CCM) AND OF 3-ETHOXYCARBONYL-BETA-CARBOLINE (BETA-CCE) [J].
SETTIMJ, G ;
DELGIUDICE, MR ;
FERRETTI, R ;
GATTA, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (05) :1391-1397
[27]   DIRECTED ORTHO METALATION - TERTIARY AMIDE AND O-CARBAMATE DIRECTORS IN SYNTHETIC STRATEGIES FOR POLYSUBSTITUTED AROMATICS [J].
SNIECKUS, V .
CHEMICAL REVIEWS, 1990, 90 (06) :879-933
[28]   DEPROTECTION OF ARENESULFONAMIDES WITH SAMARIUM IODIDE [J].
VEDEJS, E ;
LIN, SZ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1602-1603
[29]   The synthesis of aminopyridines: A method employing palladium-catalyzed carbon-nitrogen bond formation [J].
Wagaw, S ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7240-7241
[30]  
YAJIMA H, 1978, CHEM PHARM BULL, V26, P3752