The Photochemistry of Benzotriazole Derivatives. Part 2: Photolysis of 1-Substituted Benzotriazole Arylhydrazones: New Route to Phenanthridin-6-yl-2-phenyldiazines

被引：7
作者：
Al-Jalal, Nader A. [1 ]
Ibrahim, Maher R. [1 ]
Al-Awadi, Nouria A. [1 ]
Elnagdi, Mohamed H. [1 ]
机构：
[1] Kuwait Univ, Dept Chem, Fac Sci, Safat 13060, Kuwait
来源：
MOLECULES | 2011年 / 16卷 / 12期
关键词：
1,2,3-benzotriazole; phenanthridin-6-yl-2-phenyldiazine; phenanthridin-6(5H)-one; 1-anilinobenzimidazole; 1H-benzimidazole; 2-benzoyl-1H-benzoxazole; photolysis; GAS-PHASE THERMOLYSIS; PYROLYSIS;
D O I：
10.3390/molecules161210256
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Irradiation of 1-substituted benzotriazole arylhydrazones 3a-c, 4a,b and 5a,b with a 16 W low pressure mercury arc-lamp (254 nm) for 24 h gave phenanthridin-6-yl-2-phenyldiazines 9a-c, phenanthridin-6(5H)-ones 10a-c, 1-anilinobenzimidazoles 11a-c, 2-aryl-1H-benzimidazoles 12a-c, 1-arylamino-1H-benzimidazol-2-carboxylic acid ethyl esters 14a,b, 1-aryl-1H, 9H-benzo [4,5][1,2,3] triazolo[1,2-a]tetrazole-3-carboxylic acid ethyl esters 16a,b, 1-arylamino-2-benzoylbenzimidazoles 18a,b and 2-benzoylbenzoxazole 21.
引用
收藏
页码：10256 / 10268
页数：13
相关论文
共 19 条
  • [1] Gas-phase thermolysis of benzotriazole derivatives.: Part 4.: Pyrolysis of 1-acylbenzotriazole phenylhydrazones.: Interesting direct routes towards N-aminobenzimidazoles
    Al-Awadi, Hanan
    Ibrahim, Maher R.
    Al-Awadi, Nouria A.
    Ibrahim, Yehia A.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (03) : 723 - 727
  • [2] Gas-phase thermolysis of benzotriazole derivatives. Part 3: Kinetic and mechanistic evidence for biradical intermediates in pyrolysis of aroylbenzotriazoles and related compounds
    Al-Awadi, NA
    George, BJ
    Dib, HH
    Ibrahim, MR
    Ibrahim, YA
    El-Dusouqui, OME
    [J]. TETRAHEDRON, 2005, 61 (34) : 8257 - 8263
  • [3] Al-Jalal N., 2011, ARKIVOC, Vx, P288
  • [4] Photochemical study of tris(benzotriazol-1-yl)methane
    Androsov, Dmitry A.
    Neckers, Douglas C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) : 1148 - 1152
  • [5] Photochemistry of benzotriazole: An unprecedented tautomer-selective intermolecular [2+2] photocycloaddition
    Booker-Milburn, KI
    Wood, PM
    Dainty, RF
    Urquhart, MW
    White, AJ
    Lyon, HJ
    Charman, JPH
    [J]. ORGANIC LETTERS, 2002, 4 (09) : 1487 - 1489
  • [6] CYANOCYCLOPENTADIENES BY PYROLYSIS OF ISATINS AND 1H-BENZOTRIAZOLES
    CROW, WD
    WENTRUP, C
    [J]. CHEMICAL COMMUNICATIONS, 1968, (17) : 1026 - &
  • [7] Gas-phase thermolysis of benzotriazole derivatives.: Part 2:: Synthesis of benzimidazo[1,2-b]cinnolines, a novel heterocyclic ring system, by pyrolysis of benzotriazole derivatives.: Kinetic and mechanistic study
    Dib, HH
    Al-Awadi, NA
    Ibrahim, YA
    El-Dusouqui, OME
    [J]. TETRAHEDRON, 2003, 59 (47) : 9455 - 9464
  • [8] General method for the synthesis of substituted phenanthridin-6(5H)-ones using a KOH-mediated anionic ring closure as the key step
    Dubost, Emmanuelle
    Magnelli, Rosa
    Cailly, Thomas
    Legay, Remi
    Fabis, Frederic
    Rault, Sylvain
    [J]. TETRAHEDRON, 2010, 66 (27-28) : 5008 - 5016
  • [9] HUBERT AJ, 1969, J CHEM SOC C, V10, P1334
  • [10] Properties and synthetic utility of N-substituted benzotriazoles
    Katritzky, AR
    Lan, XF
    Yang, JZ
    Denisko, OV
    [J]. CHEMICAL REVIEWS, 1998, 98 (02) : 409 - 548
12