New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives

被引：0
|
作者：
A. A. Harutyunyan
机构：
[1] National Academy of Sciences of Armenia,Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry
来源：
Russian Journal of Organic Chemistry | 2016年 / 52卷
关键词：
D O I：
暂无
中图分类号：
学科分类号：
摘要：
The reactions of benzene-1,2-diamine with 5-substituted 2-(alkylsulfanyl)-4-methylpyrimidin-6(1H)-ones and 2-(propylsulfanyl)- and 5-iodo-2-(propylsulfanyl)-3,4-dihydroquinazolines at 175–185°C under solvent-free conditions unexpectedly afforded benzo[4,5]imidazo[1,2-a]pyrimidine, benzo[4,5]imidazo[2,1-b]-quinazoline, and 2,2′-(benzene-1,2-diyldiimino)bis[pyrimidin-4(3H)-ones]. The described reaction is the first example of synthesis of these heterocyclic systems by fusion of benzimidazole to pyrimidine or quinazoline and is likely to follow ANRORC mechanism.
引用
收藏
页码：1012 / 1017
页数：5
相关论文
共 50 条
  • [1] New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives
    Harutyunyan, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (07) : 1012 - 1017
  • [2] Synthesis of Benzo[4,5]imidazo[1,2-a]naphthyridine and Benzo[4,5]imidazo[2,1-a]isoquinoline Derivatives Catalyzed by CuI/L-Proline
    Dong, Fang
    Pan, Wan-Chen
    Liu, Jian-Quan
    Wang, Xiang-Shan
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (02) : 465 - 474
  • [3] Synthesis and biological evaluation of benzo[4,5]imidazo[1,2-c] pyrimidine and benzo[4,5]imidazo[1,2-a]pyrazine derivatives as anaplastic lymphoma kinase inhibitors
    Tardy, Sebastien
    Orsato, Alexandre
    Mologni, Luca
    Bisson, William H.
    Donadoni, Carla
    Gambacorti-Passerini, Carlo
    Scapozza, Leonardo
    Gueyrard, David
    Goekjian, Peter G.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (04) : 1303 - 1312
  • [4] Benzo[4,5]imidazo[1,2-a]pyridines and benzo[4,5]imidazo[1,2-a]pyrimidines: recent advancements in synthesis of two diversely important heterocyclic motifs and their derivatives
    Debnath, Saradindu
    Parveen, Syaleena
    Pradhan, Priyankar
    Das, Ipsita
    Das, Tapas
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (22) : 10504 - 10534
  • [5] Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo [4,5] imidazo[1,2-a] pyridines and benzo[4,5] imidazo[2,1-a] isoquinolines
    Yang, Byeong Woo
    Pham Duy Quang Dao
    Yoon, Nam Sik
    Cho, Chan Sik
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 851 : 136 - 142
  • [6] Simple synthesis of substituted benzo[4,5]imidazo[1,2-a]pyridines
    R. S. Begunov
    G. A. Ryzvanovich
    S. I. Firgang
    Russian Journal of Organic Chemistry, 2004, 40 : 1694 - 1696
  • [7] Simple synthesis of substituted benzo[4,5]imidazo[1,2-a]pyridines
    Begunov, RS
    Ryzvanovich, GA
    Firgang, SI
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (11) : 1694 - 1696
  • [8] Synthesis of benzo[4,5]imidazo[2,1-a]phthalazines
    Shubin, KM
    Kuznetsov, VA
    Galishev, VA
    TETRAHEDRON LETTERS, 2004, 45 (07) : 1407 - 1408
  • [9] Synthesis of benzo[4,5]imidazo[2,1-a]phthalazines
    V. A. Kuznetsov
    K. M. Shubin
    M. L. Petrov
    Russian Journal of Organic Chemistry, 2004, 40 : 1702 - 1704
  • [10] Benzo[4,5] imidazo[2,1-b] quinazolin-12-ones and benzo[4,5] imidazo[1,2-a] pyrido[2,3-d]-pyrimidine-5-ones by a sequential N-acylation-SNAr reaction
    Kumar, Krishna
    Muddala, Nagendra Prasad
    Bunce, Richard
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
12345