A novel approach to 2-arylated quinolines: Electrocyclization of alkynyl imines via vinylidene complexes

被引：111

作者：

Sangu, K ^{[1
]}

Fuchibe, K ^{[1
]}

Akiyama, T ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 03期

关键词：

D O I：

10.1021/ol036190a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkynyl imines underwent [4 + 2] electrocyclization in the presence of 20 mol % W(CO)(5)(THF) to give 2-arylated quinolines in good yields. A deuterium labeling study suggests that the reaction proceeds via a tungsten vinylidene complex.

引用

页码：353 / 355

页数：3

共 26 条

[1] Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines
Amii, H
Kishikawa, Y
Uneyama, K
[J]. ORGANIC LETTERS, 2001, 3 (08) : 1109 - 1112
[2] ORGANOMETALLIC CHEMISTRY OF VINYLIDENE AND RELATED UNSATURATED CARBENES
BRUCE, MI
[J]. CHEMICAL REVIEWS, 1991, 91 (02) : 197 - 257
[3] BRUCE MI, 1983, ADV ORGANOMET CHEM, V22, P59
[4] Metal vinylidenes in catalysis
Bruneau, C
Dixneuf, PH
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (04) : 311 - 323
[5] Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis
Cho, CS
Kim, BT
Kim, TJ
Shim, SC
[J]. CHEMICAL COMMUNICATIONS, 2001, (24) : 2576 - 2577
[6] Quinoline alkaloids of Orixa japonica
Funayama, S
Murata, K
Noshita, T
[J]. HETEROCYCLES, 2001, 54 (02) : 1139 - +
[7] STEREOSPECIFIC SYNTHESIS, ASSIGNMENT OF ABSOLUTE-CONFIGURATION, AND BIOLOGICAL-ACTIVITY OF THE ENANTIOMERS OF 3-[[[3-[2-(7-CHLOROQUINOLIN-2-YL)-(E)-ETHENYL]PHENYL][[3-(DIMETHYLAMINO)-3-OXOPROPYL]THIO]METHYL]THIO]PROPIONIC ACID, A POTENT AND SPECIFIC LEUKOTRIENE-D4 RECEPTOR ANTAGONIST
GAUTHIER, JY
JONES, T
CHAMPION, E
CHARETTE, L
DEHAVEN, R
FORDHUTCHINSON, AW
HOOGSTEEN, K
LORD, A
MASSON, P
PIECHUTA, H
PONG, SS
SPRINGER, JP
THERIEN, M
ZAMBONI, R
YOUNG, RN
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) : 2841 - 2845
[8] Novel synthesis of pentacarbonylbenzopyranylidenetungsten(0) complexes and their Diels-Alder reaction with electron-rich alkenes
Iwasawa, N
Shido, M
Maeyama, K
Kusama, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) : 10226 - 10227
[9] A novel reaction for annulation onto α,β-unsaturated ketones:: W(CO)5•L promoted exo- and endo-selective cyclizations of ω-acetylenic silyl enol ethers prepared by 1,4-addition of propargyl malonate to enones
Iwasawa, N
Maeyama, K
Kusama, H
[J]. ORGANIC LETTERS, 2001, 3 (24) : 3871 - 3873
[10] Jones G., 1984, COMPREHENSIVE HETERO, V2, P395

← 1 2 3 →