Synthesis of 2-(buta-1,3-diynyl)-N,N-dimethylanilines using reductive methylation step

被引：4
|
作者：
Kulyashova, Alexandra E. [1 ]
Mikheeva, Elena V. [1 ]
Danilkina, Natalia A. [1 ]
Balova, Irina A. [1 ]
机构：
[1] St Petersburg State Univ, Inst Chem, St Petersburg 198504, Russia
来源：
MENDELEEV COMMUNICATIONS | 2014年 / 24卷 / 02期
关键词：
ELECTROPHILIC CYCLIZATION; ACETYLENE ZIPPER; INDOLE; HETEROCYCLES; SYSTEMS;
D O I：
10.1016/j.mencom.2014.03.013
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Synthesis of 2-(buta-1,3-diynyl)-N,N-dimethylanilines based on reductive methylation of ortho-iodoanilines using CH2O-NaBH3CN and coupling with terminal diacetylens was developed. Altered sequence including dimethylation of 2-(buta-1,3-diynyl)anilines was also successfully achieved and gave higher overall yields in the case of anilines without acceptor substituent in the ring.
引用
收藏
页码：102 / 104
页数：3
相关论文
共 50 条
  • [1] Access to 2,3-bis(buta-1,3-diynyl)pyridines
    Sorokoumov, Viktor N.
    Popik, Vladimir V.
    Balova, Irina A.
    MENDELEEV COMMUNICATIONS, 2011, 21 (01) : 19 - 20
  • [2] Functionalized buta-1,3-diynyl-N-methylpyrazoles by sequential "diacetylene zipper" and Sonogashira coupling reactions
    Govdi, Anastasiya I.
    Kulyashova, Alexandra E.
    Vasilevsky, Sergey F.
    Balova, Irina A.
    TETRAHEDRON LETTERS, 2017, 58 (08) : 762 - 765
  • [3] Synthesis, Characterization and Optoelectronic Properties of Dimeric and Polymeric Metallaynes Derived from 3,6-Bis(buta-1,3-diynyl)-9-butylcarbazole
    Li Liu
    Wai-Yeung Wong
    Suk-Yue Poon
    Kok-Wai Cheah
    Journal of Inorganic and Organometallic Polymers and Materials, 2005, 15 : 555 - 567
  • [4] Effects of reducing structural symmetry on mesophase behaviour: the synthesis and characterization of the 2-alkoxy-6[4-(4-alkoxyphenyl)buta-1,3-diynyl]naphthalenes
    Hsu, HF
    Lin, WC
    Lai, YH
    Lin, SY
    LIQUID CRYSTALS, 2003, 30 (08) : 939 - 944
  • [5] Synthesis, characterization and optoelectronic properties of dimeric and polymeric metallaynes derived from 3,6-bis(buta-1,3-diynyl)-9-butylcarbazole
    Liu, Li
    Wong, Wai-Yeung
    Poon, Suk-Yue
    Cheah, Kok-Wai
    JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2005, 15 (04) : 555 - 567
  • [6] trans-bis[1,2-bis(diphenylphosphino)ethane-κ2P,P′]bis[4-(trimethylsilyl)buta-1,3-diynyl]ruthenium(II) and trans-bis[1,2-bis(diphenylphosphino)ethane-κ2P,P′]bis(buta-1,3-diynyl)ruthenium(II)
    Anderson, JN
    Brookes, NJ
    Coe, BJ
    Coles, SJ
    Light, ME
    Hursthouse, MB
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2003, 59 : M215 - M217
  • [7] SUBSTITUTED N,N-DIMETHYLANILINES CONTAINING AN ORTHO-TRIFLUOROMETHYL GROUP - SYNTHESIS OF N,N-DIMETHYL-2-TRIFLUOROMETHYLANILINE
    HEPWORTH, JD
    JONES, P
    HALLAS, G
    SYNTHESIS-STUTTGART, 1974, (12): : 874 - 876
  • [8] Synthesis of 3,3′-disubstituted-2,2′-biindolyls through sequential palladium-catalysed reactions of 2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino)-phenyl]-buta-1,3-diynyl)-phenyl)-acetamide with organic halides/triflates
    Abbiati, G
    Arcadi, A
    Beccalli, E
    Bianchi, G
    Marinelli, F
    Rossi, E
    TETRAHEDRON, 2006, 62 (13) : 3033 - 3039
  • [9] Stereoselective synthesis of substituted 2-(diethylphosphonyl)-4-(trimethylsilyl)buta-1,3-dienes
    Chevalier, F
    Al-Badri, H
    Collignon, N
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1997, 134 (8-9): : 801 - 807
  • [10] Preparation of buta-1,3-diynyl complexes of platinum(II) and their use in the construction of neutral molecular squares:: synthesis, structural and theoretical characterisation of cyclo-{Pt(μ-CCCC)(dppe)}4 and related chemistry
    Bruce, MI
    Costuas, K
    Halet, JF
    Hall, BC
    Low, PJ
    Nicholson, BK
    Skelton, BE
    White, AH
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (03): : 383 - 398
12345