Multicomponent Approach for the Synthesis of Phenanthridine and Acridine Ring Systems via the Coupling of Fischer Carbene Complexes with Heteroaromatic o-Alkynyl Carbonyl Derivatives

被引：11

作者：

Jana, Gouranga P. ^{[1
]}

Mukherjee, Soumita ^{[1
]}

Ghorai, Binay K. ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2010年 / 18期

关键词：

azaisobenzofuran; heterocycles; Diels-Alder reaction; chromium; carbene complexes; HETEROCYCLIC-ANALOGS; FUSED PYRIDINES; ISOQUINOLINES; GENERATION; QUINOLINES; CHEMISTRY; VERSATILE; TANDEM;

D O I：

10.1055/s-0030-1258180

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot multicomponent synthesis of phenanthridine and acridine derivatives is described. This method includes the in situ generation of furo[3,4-c]isoquinoline and furo[3,4-b]quinoline intermediates by the coupling of heteroaromatic o-alkynyl carbonyl derivatives with Fischer carbene complexes and subsequent trapping of these intermediates by suitable dienophiles.

引用

页码：3179 / 3187

页数：9

共 8 条

[1] Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives
Mukherjee, Soumita
Jana, Gouranga P.
Ghorai, Binay K.
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (25) : 4100 - 4106
[2] One-step convergent synthesis of the steroid ring system via the coupling of γ,δ-unsaturated Fischer carbene complexes with O-ethynylbenzaldehyde.
Ghorai, BK
Herndon, JW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U112 - U112
[3] One-step convergent synthesis of the steroid ring system via the coupling of γ,δ-unsaturated Fischer carbene complexes with o-ethynylbenzaldehyde
Ghorai, BK
Herndon, JW
Lam, YF
ORGANIC LETTERS, 2001, 3 (22) : 3535 - 3538
[4] Synthesis of o-quinoidal furanopyrones. and thienopyrones from coupling of 3-alkynyl-2-furancarboxaldehydes with Fischer carbene complexes.
Herndon, JW
Zhang, YS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U149 - U149
[5] Synthesis of furano[2,3-c]-pyran-3-one and thieno[2,3-c]-pyran-3-one derivatives through the coupling of 3-alkynyl-2-heteroaromatic carboxaldehydes with Fischer carbene complexes
Zhang, YS
Herndon, JW
TETRAHEDRON LETTERS, 2001, 42 (05) : 777 - 779
[6] 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
[7] Synthesis of furano[2,3-c]pyran-3-one and thieno[2,3-c]pyran-3-one derivatives through the coupling of 3-alkynyl-2-heteroaromatic carboxaldehydes with Fischer carbene complexes:: Total synthesis of a Baccharis-derived cadinene derivative
Zhang, YS
Herndon, JW
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12): : 4177 - 4185
[8] SILICON-CONTAINING CARBENE COMPLEXES .12. SYNTHESIS OF SMALL ORGANIC RING-SYSTEMS FROM ALKOXY-SUBSTITUTED OR ALKYLTHIO-SUBSTITUTED SILYLCARBENE COMPLEXES (CO)5MC(XET)SIR3 (M = CR, MO, W AND X = O, S) AND THEIR KETENE DERIVATIVES R3SI(ETX)C=C=O
KRON, J
SCHUBERT, U
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 373 (02) : 203 - 219

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