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
  • [1] Silver-Catalyzed Direct Regioselective C3 Phosphonation of 4H-pyrido[1,2-a]pyrimidin-4-ones With H-phosphites
    Guo, Lina
    Su, Meiyun
    Zhan, Haiying
    Liu, Wenjie
    Wang, Shaohua
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (07) : 1660 - 1664
  • [2] SYNTHESIS OF HALOGENATED 4H-PYRIDO[1,2-a]PYRIMIDIN-4-ONES
    Molnar, Annamaria
    Faigl, Ferenc
    Podanyi, Benjamin
    Finta, Zoltan
    Balazs, Laszlo
    Hermecz, Istvan
    HETEROCYCLES, 2009, 78 (10) : 2477 - 2488
  • [3] ELECTRONIC-STRUCTURE OF 4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONES
    HORVATH, G
    HERMECZ, I
    HORVATH, A
    PONGORCSAKVARI, M
    PUSZTAY, L
    KISS, AI
    CZAKO, L
    ABDIRIZAK, OH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (02) : 481 - 489
  • [4] SYNTHESIS AND GASTROPROTECTIVE ACTIVITY OF 4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONES
    HERMECZ, I
    SIPOS, J
    VASVARIDEBRECZY, L
    GYIRES, K
    KAPUI, Z
    ACTA PHYSIOLOGICA HUNGARICA, 1992, 80 (1-4) : 225 - 235
  • [5] Selective C3 Functionalization of 4H-Pyrido[1,2-a]pyrimidin-4-Ones via Glyoxylic Acid: Tuning Products with Temperature and Solvents
    Shaikh, Arbaz Sujat
    Kumar, Ashish
    Makhal, Priyanka N.
    Ikhe, Akanksha Sanjayrao
    Bhale, Nagesh
    Dikundwar, Amol G.
    Kaki, Venkata Rao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [6] Palladium-catalyzed direct alkenylation of 2-methyl-4H-pyrido[1,2-a]pyrimidin-4-ones using oxygen as the oxidant
    Lv, Junliang
    Liang, Ying
    He, Peiling
    Cai, Zhihao
    Liu, Jianwen
    Huang, Fengxi
    RSC ADVANCES, 2015, 5 (46) : 36171 - 36174
  • [7] Regioselective C(sp2)3-H thiocyanation of substituted 4H-pyrido[1,2-a]pyrimidin-4-ones and its derivatizations
    Roy, Sanjay
    Ghosh, Prasanjit
    Ghosh, Shibaji
    Mondal, Samir K.
    Mandal, Anirban
    Das, Sajal
    CHEMISTRYSELECT, 2023, 8 (37):
  • [8] Metal free C-3 chalcogenation (sulfenylation and selenylation) of 4H-pyrido[1,2-a]pyrimidin-4-ones
    Ghosh, Prasanjit
    Chhetri, Gautam
    Das, Sajal
    RSC ADVANCES, 2021, 11 (17) : 10258 - 10263
  • [10] REACTION OF 4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONES WITH N-BROMOSUCCINIMIDE
    SATTI, NK
    KHAJURIA, RK
    SURI, OP
    ATAL, CK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1984, 23 (11): : 1117 - 1118