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
收藏
页码：6467 / 6471
页数：5
相关论文
共 50 条
  • [41] Structural snapshots in the copper(II) induced azide-nitrile cycloaddition: effects of peripheral ligand substituents on the formation of unsupported μ1,1-azido vs. μ1,4-tetrazolato bridged complexes
    Sommer, Michael G.
    Rechkemmer, Yvonne
    Suntrup, Lisa
    Hohloch, Stephan
    van der Meer, Margarethe
    van Slageren, Joris
    Sarkar, Biprajit
    DALTON TRANSACTIONS, 2016, 45 (44) : 17770 - 17781
  • [42] Efficient synthesis of [1,3]oxazino[2,3-a]quinoline derivatives by a novel 1,4-dipolar cycloaddition involving a quinoline-DMAD zwitterion and carbonyl compounds
    Nair, Vijay
    Devipriya, S.
    Eringathodi, Suresh
    TETRAHEDRON LETTERS, 2007, 48 (21) : 3667 - 3670
  • [43] CYCLOADDITION REACTIONS OF CUMULENES .4. NOVEL MODE OF REACTION OF AZOMETHINE OXIDES WITH 1,1-DIMETHYLALLENE - FORMATION OF A SUBSTITUTED PIPERIDIN-4-ONE
    CUM, G
    SINDONA, G
    UCCELLA, N
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (07): : 719 - 721
  • [44] Copper catalyzed 1,3-dipolar cycloaddition reaction of azides with N-(2-trifluoroacetylaryl)propargylamines A mild entry to novel 1,4-disubstituted-[1,2,3]-triazole derivatives
    Lamarque, Jean-Florent
    Lamarque, Christophe
    Lassara, Sandrine
    Medebielle, Maurice
    Molette, Jerome
    David, Emilie
    Pellet-Rostaing, Stephane
    Lemaire, Marc
    Okada, Etsuji
    Shibata, Dai
    Pilet, Guillaume
    JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (09) : 788 - 798
  • [45] Synthesis, Crystal Structure, Antibacterial and Antituberculosis Activities of Novel Thieno[2,3-b][1,4] dithiine-1,1-dioxide Derivatives
    El-Abadelah, Mustafa M.
    Al Ma'aiteh, Ata'a alhadi T. A.
    Al-Soud, Yaseen A.
    Zahra, Jalal A.
    Khanfar, Monther A.
    Al Saoud, Hussam A.
    van Geelen, Lasse
    Kalscheuer, Rainer
    Stark, Holger
    JORDAN JOURNAL OF CHEMISTRY, 2025, 20 : 27 - 39
  • [46] Synthesis, Crystal Structure, Antibacterial and Antituberculosis Activities of Novel Thieno[2,3-b] [1,4] dithiine-1,1-dioxide Derivatives
    El-Abadelah, Mustafa M.
    Al Ma'aiteh, Ata'a alhadi T. A.
    Al-Soud, Yaseen A.
    Zahraa, Jalal A.
    Khanfar, Monther A.
    Al Saoud, Hussam A.
    van Geelen, Lasse
    Kalscheuer, Rainer
    Stark, Holger
    JORDAN JOURNAL OF CHEMISTRY, 2025, 20 (01) : 27 - 39
  • [47] FORMATION OF A CYCLIC SULFENIC ESTER DURING PHOTOCHEMICAL DECOMPOSITION OF 2,5-DIPHENYL-1,4-DITHIIN-1-OXIDE - A NOVEL CASE OF RING EXPANSION
    GAJUREL, CL
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (03): : 319 - 320
  • [48] Photochemistry of 1,4-Dihydropyridine Derivatives: Diradical Formation, Delocalization and Trapping as a Route to Novel Tricyclic and Tetracyclic Nitrogen Heterocyclic Ring Systems
    Al-Jalal, Nader A.
    Ibrahim, Yehia A.
    Al-Awadi, Nouria A.
    Ibrahim, Maher R.
    Sayed, Osama M.
    MOLECULES, 2016, 21 (07):
  • [49] Efficient Synthesis of [1,3]Oxazino[3,2-f]phenanthridine Derivatives by a Novel 1,4-Dipolar Cycloaddition Involving a Phenanthridine-Dimethyl Acetylenedicarboxylate Zwitterion and Aromatic Aldehydes
    Li, Ming
    Pan, Lei
    Wen, Li-Rong
    HELVETICA CHIMICA ACTA, 2011, 94 (01) : 169 - 177
  • [50] KETENEDITHIOACETALS .39. NOVEL SOLVOLYTIC REARRANGEMENTS OF 1,1-BIS-(METHYLTHIO)-2,4-DIMETHYL-5-ARYL (OR STYRYL)-1,4-PENTADIEN-3-OLS TO CYCLOPENTENONE DERIVATIVES
    ASOKAN, CV
    HIRIYAKKANAVAR
    JUNJAPPA, H
    TETRAHEDRON LETTERS, 1985, 26 (08) : 1087 - 1090
12345