Synthesis and properties of bis(2-heteroaryl)borane derivatives

被引：0
|
作者：
Köhler, T [1 ]
Faderl, J [1 ]
Pritzkow, H [1 ]
Siebert, W [1 ]
机构：
[1] Heidelberg Univ, Inst Anorgan Chem, D-69120 Heidelberg, Germany
来源：
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY | 2002年 / 11期
关键词：
boranes; porphyrinogens; lithiation; Grignard reaction; bromination;
D O I：
暂无
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The reaction of (isopropyloxy)bis(2-thienyl)borane (1d) with Grignard reagents leads to methylbis(2-thienyl)borane (1e) and to phenylbis(2-thienyl)borane (1f). Treatment of mono-lithiated heterocycles with dichloroboranes yields the bis(2-heteroaryl)boranes 1b, 1c, and 3a, which are dibrominated with NBS to give the 5,5'-dibromo products 1b', 2a', and 3a'. NMR spectroscopic and MS data confirm the composition of the compounds. The [2 + 2] cyclization of the dibromo derivatives yields, in the case of 2a', the macrocycle 4b, as confirmed by HR-MS data. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
引用
收藏
页码：2942 / 2946
页数：5
相关论文
共 50 条
  • [1] Synthesis and tautomerism of 2-aryl- and 2-heteroaryl derivatives of benzimidazole
    Lee, ISH
    Jeoung, EH
    Lee, CK
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (06) : 1711 - 1716
  • [2] SYNTHESIS AND ANTIVIRAL EFFECTS OF 2-HETEROARYL SUBSTITUTED ADENOSINE AND 8-HETEROARYL SUBSTITUTED GUANOSINE DERIVATIVES
    PERSSON, T
    GRONOWITZ, S
    HORNFELDT, AB
    JOHANSSON, NG
    BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (10) : 1377 - 1382
  • [3] Asymmetric Synthesis of 2-Heteroaryl Cyclic Amines: Total Synthesis of (-)-Anabasine
    Sallio, Romain
    Lebrun, Stephane
    Gigant, Nicolas
    Gillaizeau, Isabelle
    Deniau, Eric
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (20) : 4381 - 4388
  • [4] Design, Synthesis and Evaluation of Hybrid 2-Heteroaryl Benzimidazole-Chalcone Derivatives as Anticancer Agents
    Kumar, Gajula Shyam
    Rathnakar, Bethi
    Gattu, Sridhar
    Jadav, Surender Singh
    Rameshwar, Nimma
    Boyapati, Shireesha
    Satyanarayana, Mavurapu
    LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (10) : 766 - 776
  • [5] Syntheses of octa(2-heteroaryl) azaphthalocyanines
    Morkved, EH
    Ossletten, H
    Kjosen, H
    Bjorlo, O
    JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 2000, 342 (01): : 83 - 86
  • [6] Synthesis and antitumour activity of new derivatives of flavone-8-acetic acid (FAA). Part 3: 2-heteroaryl derivatives
    Aitken, RA
    Bibby, MC
    Bielefeldt, F
    Double, JA
    Laws, AL
    Mathieu, AL
    Ritchie, RB
    Wilson, DWJ
    ARCHIV DER PHARMAZIE, 1998, 331 (12) : 405 - 411
  • [7] 2-HETEROARYL 2-SUBSTITUTED PHENYLKETONE DERIVATIVES AND THEIR INHIBITORY ACTIVITY ON PLATELET-AGGREGATION
    HSU, LY
    LEE, CF
    CHOU, TC
    DING, YA
    JOURNAL OF PHARMACY AND PHARMACOLOGY, 1995, 47 (09) : 762 - 767
  • [8] A NEW APPROACH TO N-ARYL-(2-HETEROARYL)IMIDATES AND N-(2-HETEROARYL)IMIDATES FROM CHROMIUM CARBENES AND SULFILIMINES
    ALCAIDE, B
    DOMINGUEZ, G
    PLUMET, J
    SIERRA, MA
    ORGANOMETALLICS, 1991, 10 (01) : 11 - 12
  • [9] Chemoenzymatic synthesis of novel 1,4-disubstituted 1,2,3-triazole derivatives from 2-heteroaryl substituted homopropargyl alcohols
    Buyukadali, Nalan Nuriye
    Seven, Semih
    Aslan, Nezir
    Yenidede, Duygu
    Gumus, Aysegal
    TETRAHEDRON-ASYMMETRY, 2015, 26 (21-22) : 1285 - 1291
  • [10] 2-Heteroaryl Benzimidazole Derivatives as Melanin Concentrating Hormone Receptor 1 (MCH-R1) Antagonists
    Lim, Chae Jo
    Kim, Jeong Young
    Lee, Byung Ho
    Oh, Kwang-Seok
    Yi, Kyu Yang
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (08) : 2305 - 2310
12345