Regioselective C3 Alkenylation of 4H-pyrido[1,2-a] pyrimidin-4-ones via Palladium-Catalyzed C-H Activation

被引:27
|
作者
Liu, Wenjie [1 ]
Wang, Shaohua [1 ]
Zhang, Qi [1 ]
Yu, Jingwen [1 ]
Li, Jiahe [1 ]
Xie, Zhiwei [1 ]
Cao, Hua [1 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
alkenylation; C-H activation; homogeneous catalysis; palladium; regioselectivity; EFFLUX PUMP INHIBITORS; PALLADIUM(II)-CATALYZED DIRECT ALKENYLATION; DIRECT OXIDATIVE ALKENYLATION; PSEUDOMONAS-AERUGINOSA; DEHYDROGENATIVE ALKENYLATION; INTERMOLECULAR ALKENYLATION; BOND FUNCTIONALIZATION; DIRECT ARYLATION; INDOLES; OLEFINATION;
D O I
10.1002/asia.201402455
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general and efficient palladium-catalyzed direct C3 alkenylation of 4H-pyridoA1,2-a] pyrimidin-4-ones using AgOAc/O-2 as the oxidant has been developed. A variety of 4H-pyrido[1,2-a] pyrimidin-4-ones were successfully coupled with acrylate esters, styrenes, methylvinylketone, and acrylamide in moderate to excellent yields. The reaction exhibited complete regio-and stereoselectivity. This transformation provides an attractive new approach to functionalize 4HpyridoACHTUNGTRENUNG[ 1,2-a] pyrimidin-4-ones.
引用
收藏
页码:2436 / 2439
页数:4
相关论文
共 50 条
  • [41] Direct and Regioselective C-H Alkenylation of Tetrahydropyrido[1,2-a]pyrimidines
    Cheng, Dachen
    Gallagher, Timothy
    ORGANIC LETTERS, 2009, 11 (12) : 2639 - 2641
  • [42] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
    Qi, Wenke
    Wu, Yimei
    Han, Yongxu
    Li, Yi
    CATALYSTS, 2017, 7 (11)
  • [43] Heterogeneous Cu/OMS-2 as an efficient catalyst for the synthesis of tetrasubstituted 1,4-enediones and 4H-pyrido[1,2-a]-pyrimidin-4-ones
    Zhang, Jinqi
    Meng, Xu
    Yu, Chaoying
    Chen, Gexin
    Zhao, Peiqing
    RSC ADVANCES, 2015, 5 (106): : 87221 - 87227
  • [44] Pd-catalyzed carbonylative cycloamidation of ketoimines for the synthesis of pyrido[1,2-a]pyrimidin-4-ones
    Xie, Ying
    Chen, Tengfei
    Fu, Shaomin
    Jiang, Huanfeng
    Zeng, Wei
    CHEMICAL COMMUNICATIONS, 2015, 51 (45) : 9377 - 9380
  • [45] Ligandless Palladium-Catalyzed Regioselective Direct C-H Arylation of Imidazo[1,2-a]imidazole Derivatives
    Grosse, Sandrine
    Pillard, Christelle
    Massip, Stephane
    Marchivie, Mathieu
    Jarry, Christian
    Bernard, Philippe
    Guillaumet, Gerald
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8539 - 8551
  • [46] Direct C-3-Alkenylation of Quinolones via Palladium-Catalyzed C-H Functionalization
    Li, Mingzong
    Li, Liangxi
    Ge, Haibo
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2445 - 2449
  • [47] HAT-Mediated Electrochemical C(sp2)-H Alkoxylation of Pyrido[1,2-a]pyrimidin-4-ones with Aliphatic Alcohols
    Ghosh, Subhadeep
    Biswas, Sumit
    Das, Indrajit
    CHEMCATCHEM, 2024, 16 (22)
  • [48] Hexafluoroisopropyl alcohol mediated synthesis of 2,3-dihydro-4H-pyrido[1,2-a]pyrimidin-4-ones
    Mohammad A. Alam
    Zakeyah Alsharif
    Hessa Alkhattabi
    Derika Jones
    Evan Delancey
    Adam Gottsponer
    Tianhong Yang
    Scientific Reports, 6
  • [49] NITROGEN BRIDGEHEAD COMPOUNDS .51. AUTOXIDATION OF 9-AMINOTETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONES - SYNTHESIS AND STEREOCHEMISTRY OF 9-AMINO AND 9-HYDROXY-6,7-DIHYDRO-4H-PYRIDO[1,2-A]-PYRIMIDIN-4-ONES
    BREINING, T
    HERMECZ, I
    PODANYI, B
    SESSI, J
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (05) : 1253 - 1259
  • [50] Hexafluoroisopropyl alcohol mediated synthesis of 2,3-dihydro-4H-pyrido[1,2-a] pyrimidin-4-ones
    Alam, Mohammad A.
    Alsharif, Zakeyah
    Alkhattabi, Hessa
    Jones, Derika
    Delancey, Evan
    Gottsponer, Adam
    Yang, Tianhong
    SCIENTIFIC REPORTS, 2016, 6