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 50 条

[31] Synthesis and reactivity of neutral vinylidene and σ-alkynyl complexes containing the hemilabile ligand Ph2PCH2CH2OMe -: Part 16.: Ruthenium tris(pyrazolyl)borate complexes
Pavlik, S
Gemel, C
Slugovc, C
Mereiter, K
Schmid, R
Kirchner, K
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) : 301 - 310
[32] Organic syntheses via transition metal complexes. XCVII. Mesoionic pyrrolium complexes and dihydropyrroles by cycloaddition of (non-enolizable) imines to an [(1-alkynyl)carbene]tungsten complex
Aumann, R
Yu, ZK
Frohlich, R
Zippel, F
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 1998, (11) : 1623 - 1629
[33] VINYLIDENE TRANSITION-METAL COMPLEXES .26. SYNTHESIS AND STRUCTURE OF CATIONIC CARBONYL, ALKENE, VINYLIDENE, ALKYNYL AND ALKYNE RHODIUM COMPLEXES WITH THE COMPONENT TRANS-[RH((PPR3)-PR-I)2]
NURNBERG, O
WERNER, H
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 460 (02) : 163 - 175
[34] Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines
Xiang, Yunyu
Luo, Puying
Hao, Tianxin
Xiong, Weikang
Song, Xiaolin
Ding, Qiuping
TETRAHEDRON, 2021, 79
[35] A novel synthetic approach to medium ring lactones via dienetricarbonyliron complexes
Lai, ML
Chang, SC
Hwu, CC
Yeh, MCP
TETRAHEDRON LETTERS, 1996, 37 (34) : 6149 - 6152
[36] A novel synthetic approach to medium ring lactones via dienetricarbonyliron complexes
Tetrahedron Lett, 34 (6149):
[37] Novel luminescent mixed-metal Pt-Tl-alkynyl-based complexes:: The role of the alkynyl substituent in metallophilic and η2(π•••Tl)-bonding interactions
Berenguer, JR
Forniés, J
Gil, B
Lalinde, E
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) : 785 - 795
[38] NEW CYCLOADDITION AND METATHESIS REACTIONS OF THE VINYLIDENE COMPLEXES CP(CO)2M=C=CH2 (M=MN,RE) WITH IMINES, CARBODIIMIDES, AND BENZALAZINE
KELLEY, C
MERCANDO, LA
GEOFFROY, GL
RHEINGOLD, AL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 72 - INOR
[39] Cleavage of the C= N Bond in Carbodiimides via Release of High Ring Strain: A New Strategy for the Selective Synthesis of 2-Aminoaryl Alkynyl Imines
Zhou, Yi
Chi, Yue
Zhao, Fei
Zhang, Wen-Xiong
Xi, Zhenfeng
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (09) : 2463 - 2468
[40] Conversion of iminoacyl quinolinylpalladium (II) complexes into novel oxo-pyrrolo[3,4-b] quinolines via depalladation reactions
Elgazwy, Abdel-Sattar S. Hamad
APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (01) : 32 - 43

← 1 2 3 4 5 →