Synthesis of Polysubstituted Pyrimidines through Palladium-Catalyzed Isocyanide Insertion to 2H-Azirines

被引：6
|
作者：
Saeifard, Leyla [1 ]
Amiri, Kamran [1 ]
Rominger, Frank [2 ]
Mueller, Thomas J. J. [3 ]
Balalaie, Saeed [1 ]
机构：
[1] KN Toosi Univ Technol, Peptide Chem Res Inst, Tehran 158754416, Iran
[2] Heidelberg Univ, Organ Chem Inst, D-69120 Heidelberg, Germany
[3] Heinrich Heine Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 17期
基金：
美国国家科学基金会;
关键词：
2 DISCRETE NITRILES; 2+2+2 CYCLOADDITIONS; DERIVATIVES; YNAMIDES;
D O I：
10.1021/acs.joc.3c01248
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The domino process of the palladium-catalyzedcoupling reactionof isocyanides with 2H-azirine provides various tetrasubstitutedpyrimidines via one C-C bond and two C-N bond formationswith satisfactory yields. The title compounds are obtained with goodfunctional group tolerance, high atom economy, and broad substratescopes.
引用
收藏
页码：12519 / 12525
页数：7
相关论文
共 50 条
  • [1] Palladium-Catalyzed Synthesis of Polysubstituted Pyrazoles by Ring-Opening Reactions of 2H-Azirines with Hydrazones
    Shao, Jiaan
    Shu, Ke
    Liu, Shuangrong
    Zhu, Huajian
    Zhang, Jiankang
    Zhang, Chong
    Zeng, Ling-Hui
    Chen, Wenteng
    [J]. SYNLETT, 2021, 32 (03) : 316 - 320
  • [2] Synthesis of Pyridopyrimidines by Palladium-Catalyzed Isocyanide Insertion
    Estevez, Veronica
    Van Baelen, Gitte
    Lentferink, Babette H.
    Vlaar, Tjostil
    Janssen, Elwin
    Maes, Bert U. W.
    Orru, Romano V. A.
    Ruijter, Eelco
    [J]. ACS CATALYSIS, 2014, 4 (01): : 40 - 43
  • [3] Palladium-Catalyzed C-N Bond Cleavage of 2H-Azirines for the Synthesis of Functionalized α-Amido Ketones
    Xu, Fen
    Si, Xiao-Ju
    Song, Yuan-Yuan
    Wang, Xing-Dong
    Liu, Chun-Sen
    Geng, Peng-Fei
    Du, Miao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 2200 - 2208
  • [4] Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion
    Wang, Xu
    Xiong, Wenfan
    Huang, Yubing
    Zhu, Jiayi
    Hu, Qiong
    Wu, Wanqing
    Jiang, Huanfeng
    [J]. ORGANIC LETTERS, 2017, 19 (21) : 5818 - 5821
  • [5] Palladium/Silver Cocatalyzed Divergent Dimerization of 2H-Azirines for Regioselective Synthesis of Tetrasubstituted Pyrroles and Pyrimidines
    Zhao, Yongxing
    Li, Rui
    Zhao, Qingzheng
    Yao, Jinzhong
    Miao, Maozhong
    [J]. ORGANIC LETTERS, 2023, 25 (21) : 3978 - 3983
  • [6] Palladium-Catalyzed Synthesis of 4-Aminophthalazin-1(2H)-ones by Isocyanide Insertion
    Vlaar, Tjostil
    Ruijter, Eelco
    Znabett, Anass
    Janssen, Elwin
    de Kanter, Frans J. J.
    Maes, Bert U. W.
    Orru, Romano V. A.
    [J]. ORGANIC LETTERS, 2011, 13 (24) : 6496 - 6499
  • [7] Synthesis of 2,3-Difunctionalized Benzofuran Derivatives through Palladium-Catalyzed Double Isocyanide Insertion Reaction
    Hu, Weigao
    Li, Meng
    Jiang, Guangbin
    Wu, Wanqing
    Jiang, Huanfeng
    [J]. ORGANIC LETTERS, 2018, 20 (12) : 3500 - 3503
  • [8] Multicomponent Synthesis of 4-Aminophthalazin-1(2H)-ones by Palladium-Catalyzed Isocyanide Insertion
    Vlaar, Tjostil
    Mampuys, Pieter
    Helliwell, Madeleine
    Maes, Bert U. W.
    Orru, Romano V. A.
    Ruijter, Eelco
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13): : 6735 - 6745
  • [9] External Reductant-Free Palladium-Catalyzed Reductive Insertion of Isocyanide: Synthesis of Polysubstituted Pyrroles and Its Applications as a Cysteine Probe
    Chen, Dianpeng
    Shan, Yingying
    Li, Jianming
    You, Jinmao
    Sun, Xuejun
    Qiu, Guanyinsheng
    [J]. ORGANIC LETTERS, 2019, 21 (11) : 4044 - 4048
  • [10] Divergent isoindolinone synthesis through palladium-catalyzed isocyanide C-H activation
    Zhang, Fulin
    Zhao, Ruihua
    Zhu, Lei
    Yu, Yinghua
    Liao, Saihu
    Wang, Zhi-Xiang
    Huang, Xueliang
    [J]. CELL REPORTS PHYSICAL SCIENCE, 2022, 3 (03):
12345