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
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 08期
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
  • [1] Selective synthesis of benzo[4,5]imidazo[2,1-a]isoquinolines via copper-catalyzed tandem annulation of alkynylbenzonitriles with 2-Iodoanilines
    Liu, Xiaodong
    Deng, Guobo
    Liang, Yun
    TETRAHEDRON LETTERS, 2018, 59 (29) : 2844 - 2847
  • [2] Synthesis and reactions of 5-methylthieno[2′,3′:5,6]pyrimido[2,1-a]isoindol-4(5H)-one
    Kysil, Andriy I.
    Voitenko, Zoia V.
    Wolf, Jean-Gerard
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2008, 73 (02) : 247 - 257
  • [3] SYNTHESIS OF PYRIMIDO[4',5'-4,5]THIENO[2,3-B]QUINOLIN-4(3H)-ONES
    RAJ, TT
    AMBEKAR, SY
    JOURNAL OF CHEMICAL RESEARCH-S, 1988, (02): : 50 - 50
  • [4] 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
  • [5] Synthesis of 1H-pyrazolo [4′3′:5,6] pyrimido [2,1-A]-isoindol-4(10H)-ones.: Derivatives of a new ring system
    Davoodnia, A
    Bakavoli, M
    Vahedinia, A
    Rahimizadeh, M
    Roshani, M
    HETEROCYCLES, 2006, 68 (04) : 801 - 806
  • [6] (±)-12b,13-Dihydropyrido[3″,2″:4′,5′]Thieno-[3′,2′:4,5]Pyrimido[2,1-a]Isoindole-6,8-Diones: Synthesis and Stereo Structure
    V. K. Vasilin
    D. Yu. Lukina
    T. A. Stroganova
    G. D. Krapivin
    Chemistry of Heterocyclic Compounds, 2014, 49 : 1530 - 1536
  • [7] (±)-12b,13-Dihydropyrido[3",2":4′,5′]Thieno-[3′,2′:4,5]Pyrimido[2,1-a]Isoindole-6,8-Diones: Synthesis and Stereo Structure
    Vasilin, V. K.
    Lukina, D. Yu
    Stroganova, T. A.
    Krapivin, G. D.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (10) : 1530 - 1536
  • [8] Synthesis of new pyrido[4",3":4′,5′]thieno[2′,3′:4,5]pyrimido-[2,1-B][1,3,4]thiadiazine derivatives
    Ahmed, EK
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (04) : 989 - 1000
  • [9] SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF THIENO[2',3'-4,5]PYRIMIDO[2,1-B][1,3,4]THIADIAZINE DERIVATIVES
    SANTAGATI, A
    MODICA, M
    SANTAGATI, M
    CUTULI, V
    AMORE, D
    CARUSO, A
    FARMACO, 1995, 50 (09): : 605 - 609
  • [10] Synthesis and solid-state fluorescence properties of pentacyclic 7-substituted-indeno[1',2':4,5] pyrido [2,1-a] isoindol-5-ones
    Chamas, Z.
    Marchi, E.
    Presson, B.
    Aubert, E.
    Fort, Y.
    Ceroni, P.
    Mamane, V.
    RSC ADVANCES, 2015, 5 (04): : 2715 - 2723
12345