Palladium-catalyzed [4+2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines

被引:6
|
作者
Sun, Li [1 ,2 ]
Li, Jiyu [1 ,2 ]
Wu, Yafei [1 ,2 ]
Li, Ying [1 ,2 ]
Chen, Junqi [1 ,2 ]
Xia, Xiaoye [1 ,2 ]
Yuan, Chunhao [4 ]
Guo, Hongchao [3 ]
Mao, Biming [1 ,2 ]
机构
[1] Shandong First Med Univ & Shandong Acad Med Sci, Sch Pharmaceut Sci, Jinan 250117, Shandong, Peoples R China
[2] Shandong First Med Univ & Shandong Acad Med Sci, Inst Mat Med, Jinan 250117, Shandong, Peoples R China
[3] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
[4] Shandong First Med Univ, Sch Chem & Pharmaceut Engn, Shandong Acad Med Sci, Tai An 271016, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
INHIBITORS;
D O I
10.1039/d3ob01361h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines has been successfully developed under mild reaction conditions, affording pharmacologically interesting oxazine or hydropyrimidine derivatives in high yields (up to 99% yield). Furthermore, the cycloaddition reactions could be efficiently scaled up and several synthetic transformations were accomplished for the construction of other useful 1,3-oxazine and hydropyrimidinone derivatives. A Pd-catalyzed [4+2] cycloaddition of 2-methylidenetrimethylene carbonate or methylene cyclic carbamate with sulfamate-derived cyclic imines has been successfully developed to afford oxazine or hydropyrimidine derivatives.
引用
收藏
页码:8107 / 8111
页数:5
相关论文
共 50 条
  • [21] Progress in Palladium-Catalyzed Diels-Alder [4+2] Cycloaddition Reaction
    Duan, Zebin
    Long, Yuhua
    Yang, Dingqiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (03) : 368 - 380
  • [22] Palladium-catalyzed stereoselective decarboxylative [4+2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones
    Zhang, Ke
    Zuo, Sheng
    You, Pengyuan
    Ru, Tong
    Chen, Fen-Er
    CHINESE CHEMICAL LETTERS, 2024, 35 (06)
  • [23] Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines
    Trost, Barry M.
    Silverman, Steven M.
    Stambuli, James P.
    Journal of the American Chemical Society, 2007, 129 (41): : 12398 - 12399
  • [24] Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of Vinyl Benzoxazinanones with Cyclic N-Sulfimines: Stereoselective Synthesis of Benzosulfamidate-Fused Tetrahydroquinazolines
    Mun, Dasom
    Kim, Eunjin
    Kim, Sung-Gon
    SYNTHESIS-STUTTGART, 2019, 51 (11): : 2359 - 2370
  • [25] Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with Imines
    Trost, Barry M.
    Silverman, Steven M.
    Stambuli, James P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12398 - +
  • [26] Diastereoselective Palladium-Catalyzed (3+2)-Cycloadditions from Cyclic Imines and Vinyl Aziridines
    Spielmann, Kim
    van der Lee, Arie
    de Figueiredo, Renata Marcia
    Campagne, Jean-Marc
    ORGANIC LETTERS, 2018, 20 (05) : 1444 - 1447
  • [27] Palladium-Catalyzed [4+2] Annulation of Cyclopro with Benzosilacyclobutanes
    Wang, Xichao
    Zhao, Dongbing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (04) : 1080 - 1081
  • [28] An Improvement of the Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Carbonates with Alkenes
    Jin, Yushu
    Ishizuka, Kentaro
    Kuwano, Ryoichi
    SYNLETT, 2014, 25 (17) : 2488 - 2492
  • [29] Diastereo- and enantioselective palladium-catalyzed dearomative [4+2] cycloaddition of 3-nitroindoles
    Suo, Jia-Jia
    Du, Juan
    Jiang, Yang-Jie
    Chen, Di
    Ding, Chang-Hua
    Hou, Xue-Long
    CHINESE CHEMICAL LETTERS, 2019, 30 (08) : 1512 - 1514
  • [30] Diastereo-and enantioselective palladium-catalyzed dearomative [4+2] cycloaddition of 3-nitroindoles
    Jia-Jia Suo
    Juan Du
    Yang-Jie Jiang
    Di Chen
    Chang-Hu Ding
    Xue-Long Hou
    ChineseChemicalLetters, 2019, 30 (08) : 1512 - 1514