Directed lithiation of unprotected quinolinecarboxylic acids

被引：17

作者：

Rebstock, AS ^{[1
]}

Mongin, F ^{[1
]}

Trécourt, F ^{[1
]}

Quéguiner, G ^{[1
]}

机构：

[1] IRCOF, UMR 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

关键词：

lithiation; quinolines; carboxylic acids; neighbouring group effects;

D O I：

10.1016/S0040-4039(01)02265-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithium salts of quinoline-2-carboxylic acid and 4-methoxyquinoline-2-carboxylic acid undergo deprotonation at C3 when treated with LTMP in THF at -25 and 0degreesC, respectively. The lithium salts of quinoline-3- and 4-carboxylic acids Lire more prone to nucleophilic addition; nevertheless, they are deprotonated at C4 and C3, respectively, when treated with LTMP in THF at -50degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：767 / 769

页数：3

共 50 条

[21] DIRECTED ORTHO-LITHIATION OF ALKYL ARENESULFONATES
BONFIGLIO, JN
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14): : 2833 - 2835
[22] SYNTHESIS OF ANTHRAQUINONES USING DIRECTED LITHIATION REACTION
WATANABE, M
FUKUDA, T
MIYASHITA, T
FURUKAWA, S
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1985, 105 (01): : 11 - 18
[23] o-DIRECTED LITHIATION OF ACYLATED HYDROXYTHIOPHENES
Vendina, Ineta
Parkova, Anete
Trapencieris, Peteris
HETEROCYCLES, 2014, 88 (02) : 1565 - 1572
[24] Directed ortho-lithiation on solid phase
Havez, S
Begtrup, M
Vedso, P
Andersen, K
Ruhland, T
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21): : 7418 - 7420
[25] Directed ortho lithiation of N-alkylphenylaziridines
Capriati, V
Florio, S
Luisi, R
Musio, B
ORGANIC LETTERS, 2005, 7 (17) : 3749 - 3752
[26] DIRECTED ORTHO-LITHIATION OF ALKYL ARENESULFONATES
BONFIGLIO, JN
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 192 : 52 - ORGN
[27] Ortho-directed lithiation of ω-phenoxy alcohols
Salteris, CS
Kostas, ID
Micha-Screttas, M
Heropoulos, GA
Screttas, CG
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15): : 5589 - 5592
[28] THE DIRECTED ORTHO-LITHIATION OF ARYL TETRAMETHYLPHOSPHORODIAMIDATES
WATANABE, M
DATE, M
KAWANISHI, K
HORI, T
FURUKAWA, S
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (10) : 2637 - 2643
[29] Behaviour of N-pyridylbenzamides versus benzanilides in the ortho-directed lithiation of masked aromatic carboxylic acids
Józwiak, A
Brzezinski, JZ
Plotka, MW
Szczesniak, AK
Malinowski, Z
Epsztajn, J
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) : 3254 - 3261
[30] LITHIATION OF POLYHYDRIC COMPOUNDS - SALICYLIC ACIDS
ROTGER, MC
COSTA, A
SAA, JM
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15): : 4083 - 4087

← 1 2 3 4 5 →