1,5-ELECTROCYCLIZATION OF 1-ALKYL-3-[(2Z)-2,4-DIARYL-4-OXOBUT-2-EN-1-YL]-1H-BENZIMIDAZOL-3-IUM BROMIDES

被引：2
|
作者：
Potikha, L. M. [1 ]
Turelyk, A. R. [1 ]
Kovtunenko, V. A. [1 ]
机构：
[1] Taras Shevchenko Natl Univ, UA-01033 Kiev, Ukraine
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2011年 / 47卷 / 04期
关键词：
benzimidazolium ylide; pyrido[1,2-a]benzimidazole; pyrrolo[1,2-a]benzimidazole; 1,5-electrocyclization; DERIVATIVES;
D O I：
10.1007/s10593-011-0780-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclization of 1-alkyl-3-[(2Z)-2,4-diaryl-4-oxobut-2-en-1-yl]-1H-benzimidazol-3-ium bromides occurs in the presence of MeONa at a reduced temperature of 5-10 degrees C via a 1,5-electrocyclization mechanism to give 3a,4-dihydro-3H-pyrrolo[1,2-a]benzimidazoles. These are unstable under the reaction conditions and are readily converted to {1-[2-(alkylamino)phenyl]-4-phenyl-1H-pyrrol-3-yl}(phenyl)methanones.
引用
收藏
页码：452 / 455
页数：4
相关论文
共 50 条
  • [21] (2Z)-3-(4-Chloroanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2en-1-one
    Asiri, Abdullah M.
    Al-Youbi, Abdulrahman O.
    Alamry, Khalid A.
    Faidallah, Hassan M.
    Ng, Seik Weng
    Tiekink, Edward R. T.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2157 - U1609
  • [22] Bis{2-[4-(methylsulfanyl)phenyl]-1H-benzimidazol-3-ium} tetrabromidocuprate(II) dihydrate
    Manjunatha, M. N.
    Ziaulla, Mohamed
    Sankolli, Ravish
    Begum, Noor Shahina
    Nagasundara, K. R.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : M578 - U692
  • [23] 1-{[Dimethyl(phenyl) silyl] methyl}-3-(2-phenylethyl)-1H-benzimidazol-3-ium bromide monohydrate
    Akkurt, Mehmet
    Kucukbay, Hasan
    Sireci, Nihat
    Buyukgungor, Orhan
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2718 - +
  • [24] 1-{(Z)-1-[3-(4-Bromophenoxy)propoxy]-1-(2,4-difluorophenyl)prop-1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate
    Shen, Fei
    Guo, Song
    Luan, Yuan-Yuan
    Wang, Kai
    Hu, Yong-Hong
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2010 - +
  • [25] 2-Trifluoromethyl-1H-benzimidazol-3-ium nitrate
    Liu, Ming-Liang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1012 - +
  • [26] 2-Trifluoromethyl-1H-benzimidazol-3-ium perchlorate
    Liu, Ming-Liang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2821 - +
  • [27] Bis{2-[4-(methylsulfanyl)phenyl]-1H-benzimidazol-3-ium} tetrabromidocadmate(II) ethanol monosolvate
    Manjunatha, M. N.
    Ziaulla, Mohamed
    Begum, Noor Shahina
    Nagasundara, K. R.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : M771 - U1210
  • [28] 1H-Benzimidazol-3-ium-2-carboxylate dihydrate
    Yao, Xing-Jun
    Yuan, Qian
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1399 - U569
  • [29] 1-(1H-Benzimidazol-2-yl)-3-(3-chlorophenyl) prop-2-en-1-one
    Adohi-Krou, A.
    Ouattara, M.
    Zoro-Diama, E. G.
    Akonan, L.
    Aycard, J. P.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O4761 - U5532
  • [30] Hydrogen-bonded sheets in 2-(2-aminophenyl)-1H-benzimidazol-3-ium dihydrogen phosphate
    Shylaja, S.
    Mahendra, K. N.
    Varma, K. B. R.
    Narasimhamurthy, T.
    Rathore, R. S.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2008, 64 (o361-o363): : O361 - O363
12345