Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

被引：10

作者：

Mukherjee, Soumita ^{[1
]}

Jana, Gouranga P. ^{[1
]}

Ghorai, Binay K. ^{[1
]}

机构：

[1] Bengal Engn & Sci Univ, Dept Chem, Sibpur 711103, Howrah, India

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2009年 / 694卷 / 25期

关键词：

Fischer carbene; Isoquinoline; Azaisobenzofuran; Diels-Alder reaction; Heterolignan; DIELS-ALDER REACTIONS; CONFORMATIONALLY RESTRICTED ANALOGS; CONTAINING HETEROCYCLIC-ANALOGS; 1-ARYLNAPHTHALENE LIGNANS; BENZODIAZEPINE-RECEPTOR; IRIDIUM COMPLEXES; 2-ALKYNYLBENZALDEHYDE DERIVATIVES; ELECTROCHEMICAL PROPERTIES; ASYMMETRIC CATALYSIS; GENERATION;

D O I：

10.1016/j.jorganchem.2009.08.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of Fischer carbene complex with o-alkynylpyridine carbonyl derivatives has been investigated. This involves the generation of furo[3,4-c] pyridine as transient intermediates through the coupling of o-alkynylpyridine carbonyl derivatives with carbene complex and subsequent Diels-Alder trapping with suitable dienophiles resulted in the formation of isoquinoline derivatives and the entire sequence can be run in one pot. When an olefinic tether was present, intramolecular Diels-Alder cycloaddition occurred followed by ring opening to yield tricyclic alcohols. (C) 2009 Elsevier B. V. All rights reserved.

引用

页码：4100 / 4106

页数：7

共 41 条

[1] Multicomponent Approach for the Synthesis of Phenanthridine and Acridine Ring Systems via the Coupling of Fischer Carbene Complexes with Heteroaromatic o-Alkynyl Carbonyl Derivatives
Jana, Gouranga P.
Mukherjee, Soumita
Ghorai, Binay K.
SYNTHESIS-STUTTGART, 2010, (18): : 3179 - 3187
[2] Synthesis of hydronaphthalenes through coupling of enyne-carbonyl compounds that contain pendant alkane groups with Fischer carbene complexes
Patti, Rajesh Kumar
Duan, Shaofeng
Camacho-Davila, Alejandro
Waynant, Kris
Dunn, Kenneth A.
Herndon, James W.
TETRAHEDRON LETTERS, 2010, 51 (28) : 3682 - 3684
[3] Synthesis of hydrophenanthrenes through a 'green' Fischer carbene-alkyne coupling process
Li, RT
Zhang, L
Camacho-Davila, A
Herndon, JW
TETRAHEDRON LETTERS, 2005, 46 (31) : 5117 - 5120
[4] Fischer carbene complexes of cobalt(I): Synthesis and structure
Moeng, Mmushi M.
Malan, Frederick P.
Lotz, Simon
Bezuidenhout, Daniela, I
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1252
[5] Synthesis of Isoquinolines Derivatives from o-Alkynyl Aldehydes
Li, Yubo
Zhao, Yunhui
Luo, Mingjian
Tang, Zilong
Cao, Chaotun
Deng, Keqin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (10) : 2504 - 2509
[6] Alkynylcyclopropanes from Terminal Alkynes through Consecutive Coupling to Fischer Carbene Complexes and Selective Propargylene Transfer
Barluenga, Jose
Tudela, Eva
Vicente, Ruben
Ballesteros, Alfredo
Tomas, Miguel
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2349 - 2352
[7] Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines, Fischer carbene complexes, and electron-deficient alkynes
Dhakal, Bishnu
Gamage, Lalith S. R.
Zhang, Yanshi
Herndon, James W.
TETRAHEDRON LETTERS, 2017, 58 (14) : 1403 - 1407
[8] One-Pot Three-Component Synthesis of Quinoxaline, Quinazoline, and Phenazine Ring Systems Using Fischer Carbene Complexes
Mukherjee, Soumita
Roy, Priyabrata
Ghorai, Binay K.
SYNTHESIS-STUTTGART, 2011, (09): : 1419 - 1426
[9] Synthesis and characterization of novel nitroxide organometallic Fischer-type carbene complexes
Le Poul, Pascal
Caro, Bertrand
Cabon, Nolwenn
Robin-Le Guen, Francoise
Golhen, Stephane
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 745 : 57 - 63
[10] Synthesis and structural characterization of (pyrazolyl)alkenyl Fischer carbene complexes of chromium and tungsten
Gu, KC
Chen, JZ
Zheng, ZY
Wu, SZ
Wu, XW
Han, XW
Yu, ZK
POLYHEDRON, 2005, 24 (01) : 173 - 180

← 1 2 3 4 5 →