A Highly Selective Synthesis of (E)-11-Arylidenebenzo [4′,5′] thieno [2′,3′: 4,5] Pyrimido [2,1-a] Isoindol-13(1H)-ones via Copper-Catalyzed Sonogashira Coupling and Hydroamination

被引:0
|
作者
He, Heng [1 ]
Wang, Zhen-Xu [1 ]
Zhang, Mei-Mei [1 ]
Liu, Jian-Quan [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synth Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
关键词
alkyne; benzothienopyrimidoisoindoles; copper; hydroamination; Sonogashira coupling; PARALLEL SYNTHESIS; MITIGLINIDE; RALOXIFENE; KAD-1229; AGENT; DERIVATIVES;
D O I
10.1002/ajoc.202400163
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and highly selective reaction of 2-(2-bromophenyl)-5,6,7,8-tetrahydrobenzo [4,5] thieno[2,3-d]pyrimidin-4(3H)-one and terminal alkyne has been developed under palladium-free conditions by CuI-catalyzed sequential Sonogashira coupling reaction and 5-exo-dig hydroamination reaction. A series of 11-arylidene-2,3,4,11-tetrahydrobenzo [4 ',5 ']thieno [2 ',3 ' : 4,5]pyrimido [2,1-a]isoindol-13(1H)-one derivatives with only the (E)-configuration were obtained.
引用
收藏
页数:4
相关论文
共 50 条
  • [41] Diversified Synthesis of 2-(4-Oxo[1,2,3]triazolo[1,5-a]quinoxalin-5(4H)-yl)acetamide Derivatives through Ugi-4-CR and Copper-Catalyzed Tandem Reactions
    An, Yu
    He, Huan
    Liu, Tiantian
    Zhang, Yong
    Lu, Xiaoyun
    Cai, Qian
    SYNTHESIS-STUTTGART, 2017, 49 (17): : 3863 - 3873
  • [42] Selenium-Catalyzed Oxidative C-H Amination of (E)-3-(Arylamino)-2-styrylquinazolin-4(3H)-ones: A Metal-Free Synthesis of 1,2-Diarylpyrazolo[5,1-b]quinazolin-9(1H)-ones
    Zhang, Yetong
    Shao, Yinlin
    Gong, Julin
    Zhu, Jianghe
    Cheng, Tianxing
    Chen, Jiuxi
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05) : 2798 - 2807
  • [43] Efficient and facile synthesis of 5-arylindeno[2,1:5,6]pyrido[2,3-d] pyrimidine-2,4(3H)-dione and 7-arylbenzo[h]pyrimido[4,5-b]quinoline-8,10(5H,9H)-dione under mild conditions
    Wang, Zhansheng
    Wang, Mengyao
    Xu, Shuangshuang
    Gu, Mengmeng
    Meng, Zhiying
    Li, Chuan
    Cai, Peijun
    Rong, Liangce
    SYNTHETIC COMMUNICATIONS, 2016, 46 (23) : 1887 - 1892
  • [44] Efficient Synthesis of New Pyrimido[5,4:5,6]pyrano[2,3-d]pyrimidine-2,4,6(1H,3H)-triones via the Tandem Intramolecular Pinner-Dimroth Rearrangement, and Their Antibacterial Activity
    Asadian, M.
    Davoodnia, A.
    Beyramabadi, S. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (12) : 2658 - 2663
  • [45] Synthesis and Anticancer Activity of 2-Aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-dione and 2-Aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones
    Chaban, T., I
    Matiichuk, Y. E.
    Horishny, V. Ya
    Chaban, I. G.
    Matiychuk, V. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (05) : 813 - 818
  • [46] Facile synthesis of new pyrazolo[4′,3′:5,6]pyrano[2,3-d] pyrimidin-5(1H)-ones via the tandem intramolecular Pinner-Dimroth rearrangement and their antibacterial evaluation
    Dorostkar-Ahmadi, Nadieh
    Davoodnia, Abolghasem
    Tavakoli-Hoseini, Niloofar
    Behmadi, Hossein
    Nakhaei-Moghaddam, Mahboobeh
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2019, 74 (02): : 175 - 181
  • [47] Synthesis of (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-5,10-diones
    Fedorov, A. E.
    Rodinovskaya, L. A.
    Shestopalov, A. M.
    Sigeev, A. S.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (02) : 394 - 405
  • [48] ANRORC type rearrangement/intermolecular cyclocondensation cascade of 5,6-dicyano-3-(2-oxo-2-ethyl)pyrazin-2(1H)-ones with hydrazine hydrate for the synthesis of 2-(pyrazol-3-yl)imidazo[4,5-d]pyridazines
    Mamedov, Vakhid A.
    Galimullina, Venera R.
    Qu, Zheng-Wang
    Zhu, Hui
    Syakaev, Victor V.
    Nikolaeva, Dariya V.
    Rizvanov, Il'dar Kh.
    Gubaidullin, Aidar T.
    Sinyashin, Oleg G.
    Grimme, Stefan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (09) : 2180 - 2189
  • [49] A facile access to the synthesis of highly functionalized novel 4H-pyrano [2′,3′:4,5]imidazo[1,2-a]pyridine hybrid via one-pot four-component domino reaction
    Vediyappan, Ramesh
    Devi, Natarajan Savitha
    Ajaydev, Rameshbabu
    Shanmugam, Sivakumar
    TETRAHEDRON LETTERS, 2023, 131
  • [50] One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
    Xie, Jialin
    Guo, Zhonglin
    Huang, Yuanqiong
    Qu, Yi
    Song, Hongjian
    Song, Haibin
    Liu, Yuxiu
    Wang, Qingmin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 490 - 495