Thieno[3,2-b]benzofuran - Synthesis and reactions

被引：26
|
作者：
Vachal, P
Pihera, P
Svoboda, J
机构：
[1] Department of Organic Chemistry, Prague Inst. of Chemical Technology
来源：
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 1997年 / 62卷 / 09期
关键词：
fused heterocycles; thieno[3,2-b]benzofuran; benzothieno[3,2-b]furan; electrophilic substitution; metallation;
D O I：
10.1135/cccc19971468
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Thieno[3,2-b]benzofuran was synthesized starting from benzo[b]furan-3(2H)-one or benzo[b]furan-2-carbaldehyde. Electrophilic substitution reactions such as bromination, formylation, acetylation or nitration, take place in position 2. An electron donating group in position 2 directs further electrophilic substitution into positions 3 and 6, whereas compounds with an electron acceptor in position 2 are substituted exclusively in position 6. Metallation with butyllithium took place in position 2. The H-1 and C-13 NMR signals of the title compound were fully assigned.
引用
收藏
页码：1468 / 1480
页数：13
相关论文
共 50 条
  • [41] Hole mobility in thieno[3,2-b]thiophene oligomers
    Malov, Vladimir V.
    Ghosh, Tanwistha
    Nair, Vijayakumar C.
    Maslov, Mikhail M.
    Katin, Konstantin P.
    Unni, K. N. Narayanan
    Tameev, Alexey R.
    MENDELEEV COMMUNICATIONS, 2019, 29 (02) : 218 - 219
  • [42] New Carboxamides of the Thieno[3,2-b]pyrrole Series
    Torosyan, S. A.
    Nuriakhmetova, Z. F.
    Gimalova, F. A.
    Miftakhov, M. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (10) : 1850 - 1853
  • [43] New Carboxamides of the Thieno[3,2-b]pyrrole Series
    S. A. Torosyan
    Z. F. Nuriakhmetova
    F. A. Gimalova
    M. S. Miftakhov
    Russian Journal of Organic Chemistry, 2020, 56 : 1850 - 1853
  • [44] ELECTRONIC-SPECTRA OF THIENO[3,2-B]THIOPHENE
    BERTINELLI, F
    BRILLANTE, A
    PALMIERI, P
    TALIANI, C
    JOURNAL OF CHEMICAL PHYSICS, 1977, 66 (01): : 51 - 58
  • [45] Regioselective Synthesis of Thieno[3,2-b]quinolones by Acylation/Two-Fold Buchwald-Hartwig Reactions
    Janke, Julia
    Ehlers, Peter
    Villinger, Alexander
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (43) : 7255 - 7263
  • [46] Multifunctional Benzo[4,5]thieno[3,2-b]benzofuran Derivative with High Mobility and Luminescent Properties
    Wang, Jiangfeng
    He, Yaowu
    Guo, Shenghui
    Ali, Muhammad Umair
    Zhao, Changbin
    Zhu, Yanan
    Wang, Tao
    Wang, Yunrui
    Miao, Jingsheng
    Wei, Guodan
    Meng, Hong
    ACS APPLIED MATERIALS & INTERFACES, 2021, 13 (10) : 12250 - 12258
  • [47] Synthesis of novel photochromic spiro compounds based on thieno[3,2-b]pyrroles
    Shimkin, AA
    Nikalin, DM
    Shirinian, VZ
    Krayushkin, MM
    Vorontsova, LG
    Metelitsa, AV
    Minkin, VI
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2005, 431 : 307 - 313
  • [48] THIENO[2,3-B][1]BENZOTHIOPHEN AND THIENO[3,2-B][1]BENZOTHIOPHEN .2. SUBSTITUTION REACTIONS
    CHAPMAN, NB
    HUGHES, CG
    SCROWSTO.RM
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03): : 463 - &
  • [49] One-pot approach to construct benzo[4,5]thieno[3,2-b]indoles, pyrido [3′,2′:4,5]thieno[3,2-b]indoles and pyrazino[2′,3′:4,5]thieno[3,2-b] indoles based on the Fischer indole synthesis
    Irgashev, Roman A.
    Steparuk, Alexander S.
    Rusinov, Gennady L.
    TETRAHEDRON, 2020, 76 (52)
  • [50] STUDIES IN BENZOFURO[2,3-B]AND BENZOFURO[3,2-B]BENZOFURAN SERIES .2. SYNTHESIS BY CLAISEN REARRANGEMENT OF BENZOFURO[2,3-B] AND BENZOFURO[3,2-B]BENZOFURAN DERIVATIVES - REARRANGEMENT OF BENZOFURO[3,2-B]BENZOFURAN DERIVATIVES INTO ISOMERIC BENZOFURO[2,3-B]BENZOFURANS
    RAMAH, M
    LAUDE, B
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1975, (11-1): : 2655 - 2661
12345