Isoquinoline formation by a novel photochemical intermolecular cycloaddition of 1,1-diphenylethene derivatives to 1,4-dicyanobenzene

被引：9

作者：

Ishii, H

Imai, Y

Hirano, T ^{[1
]}

Maki, S

Niwa, H

Ohashi, M

机构：

[1] Univ Electrocommun, Dept Appl Phys & Chem, Chofu, Tokyo 1828585, Japan

[2] Kanagawa Univ, Dept Mat Sci, Hiratsuka, Kanagawa 2591293, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 33期

关键词：

photochemistry; electron transfer; isoquinolines; cycloadditions;

D O I：

10.1016/S0040-4039(00)01078-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenanthrene-sensitized photoreaction of 1,1-diphenylethene (DPE) derivatives and 1,4-dicyanobenzene (DCNB) in benzene leads to a novel intermolecular cycloaddition to give isoquinoline derivatives as a novel synthetic method. The feasibility of this reaction was dependent upon the side chain structure of DPE derivatives, which would regulate the stability of radical cation DPE+. in a highly polar exciplex, and/or a contact radical ion pair, by hyperconjugation or neighboring group participation. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6467 / 6471

页数：5

共 50 条

[21] The photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction .10. Intramolecular reactions involving alk-4-enols and 1,4-dicyanobenzene
McManus, KA
Arnold, DR
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (12): : 2158 - 2169
[22] PHOTOCHEMICAL (2PI+6PI)-CYCLOADDITIONS - NOVEL 1,4-CYCLOADDITION WITH FORMATION OF BICYCLO-[2.2.2]OCTADIENE SYSTEM
HESSE, G
LECHTKEN, P
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (02) : 133 - &
[23] The photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction .11. Involving (R)-(+)-alpha-terpineol and (R)-(+)-limonene, substituting on 1,4-dicyanobenzene
Arnold, DR
Conner, DA
McManus, KA
Bakshi, PK
Cameron, TS
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (04): : 602 - 612
[24] RADICAL IONS IN PHOTOCHEMISTRY .32. PHOTOCHEMICAL NUCLEOPHILE OLEFIN COMBINATION, AROMATIC-SUBSTITUTION (PHOTO-NOCAS) REACTION .6. METHANOL, NONCONJUGATED DIENES, AND 1,4-DICYANOBENZENE
ARNOLD, DR
MCMANUS, KA
DU, XY
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (02): : 415 - 429
[25] Photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction. Part 10: Intramolecular reactions involving alk-4-enols and 1,4-dicyanobenzene
McManus, Kimberly A.
Arnold, Donald R.
Canadian Journal of Chemistry, 1995, 73 (12): : 2158 - 2169
[26] PHOTOCHEMICAL NUCLEOPHILE-OLEFIN COMBINATION, AROMATIC-SUBSTITUTION (PHOTO-NOCAS) REACTION .9. METHANOL-2,6-DIMETHYL-1,6-HEPTADIENE, AND 1,4-DICYANOBENZENE
CONNOR, DA
ARNOLD, DR
BAKSHI, PK
CAMERON, TS
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (06): : 762 - 771
[27] Highly regio- and stereoselective 1,1-cycloaddition of carbon monoxide with 1,4-dilithio-1,3-dienes. Novel synthetic methods for 3-cyclopenten-1-one derivatives
Song, QL
Chen, JL
Jin, XL
Xi, ZF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) : 10419 - 10420
[28] One-pot synthesis of novel 1,1′- and 1,4-bridged bis-thiazolidinone derivatives and their antimicrobial activity
Shaker, RM
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 149 : 7 - 14
[29] FORMATION OF 1,4-THIAZINE 1,1-DIOXIDES BY CYCLOADDITION-EXTRUSION-RING EXPANSION REACTIONS OF MESOIONIC OXAZOLONES WITH DIPHENYLTHIIRENE DIOXIDE
MATSUKUBO, H
KOJIMA, M
KATO, H
CHEMISTRY LETTERS, 1975, (11) : 1153 - 1154
[30] 1,1-Cycloaddition of oxalyl dichloride with dialkenylmetal compounds: Formation of cyclopentadienone derivatives by the reaction of 1,4,-dilithio-1,3-dienes or zirconacyclopentadienes with oxalyl chloride in the presence of CuCl
Chen, C
Xi, CJ
Jiang, YF
Hong, XY
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) : 8024 - 8025

← 1 2 3 4 5 →