Concomitant (3+3) Annulation/Fragmentation of Triazinanes with Enamines: Electrosynthesis of Multisubstituted Dihydropyrimidines

被引：0
|
作者：
Dutta, Jhilik [1 ]
Ghosh, Sayan [1 ]
Hassan, Aaliya [1 ]
De Sarkar, Suman [1 ]
机构：
[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, West Bengal, India
来源：
ORGANIC LETTERS | 2025年 / 27卷 / 11期
关键词：
ACCESS;
D O I：
10.1021/acs.orglett.5c00418
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An electro-oxidative formal (3 + 3) annulation of 1,3,5-triazinanes with enamines toward multisubstituted 1,2-dihydropyrimidines is reported. This metal-free mild protocol offers wide functional group tolerance, and heterocycles with an unexplored molecular scaffold were constructed in excellent yields. Mechanistically, the electro-oxidation of triazinane and nucleophilic reactivity of enamine result in a concomitant annulation-fragmentation process, leading to the six-membered heterocyclic product.
引用
收藏
页码：2682 / 2686
页数：5
相关论文
共 50 条
  • [21] Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
    Changgui Zhao
    Donghui Guo
    Kristin Munkerup
    Kuo-Wei Huang
    Fangyi Li
    Jian Wang
    Nature Communications, 9
  • [22] Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides
    Pan, Ting
    Gao, Xing
    Yang, Sen
    Wang, Lan
    Hu, Yimin
    Liu, Min
    Wang, Wei
    Wu, Yongjun
    Zheng, Bing
    Guo, Hongchao
    ORGANIC LETTERS, 2021, 23 (15) : 5750 - 5754
  • [23] Stereoselective synthesis of highly oxygenated cyclohexanes through a [3+3] annulation approach
    Sharma, GVM
    Prasad, TR
    Krishna, PR
    Krishnudu, K
    Rao, MHVR
    Kunwar, AC
    TETRAHEDRON-ASYMMETRY, 2000, 11 (22) : 4499 - 4507
  • [24] Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
    Zhao, Changgui
    Guo, Donghui
    Munkerup, Kristin
    Huang, Kuo-Wei
    Li, Fangyi
    Wang, Jian
    NATURE COMMUNICATIONS, 2018, 9
  • [25] Tropane and related alkaloid skeletons via a radical [3+3]-annulation process
    Colson, Eloise
    Andrez, Julie
    Dabbous, Ali
    Denes, Fabrice
    Maurel, Vincent
    Mouesca, Jean-Marie
    Renaud, Philippe
    COMMUNICATIONS CHEMISTRY, 2022, 5 (01)
  • [26] Gold-Catalyzed [3+3]-Annulation of Azomethine Imines with Propargyl Esters
    Shapiro, Nathan D.
    Shi, Yun
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) : 11654 - +
  • [27] Electrochemical [3+3] Annulation of Phenol and Hydrazone: Synthesis of 1,3,4-Oxadiazines
    Zhang, Jiahui
    Hu, Yangyang
    Ran, Ya'nan
    Liu, Huiying
    Sun, Jingwen
    Wang, Haijun
    Liu, Lei
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (08): : 2869 - 2878
  • [28] Base-Catalyzed Diastereoselective [3+3] Annulation of 3-Isothiocyanatooxindoles and Azomethine Imines
    Zhu, Gongming
    Sun, Wangsheng
    Wu, Chongyang
    Li, Guofeng
    Hong, Liang
    Wang, Rui
    ORGANIC LETTERS, 2013, 15 (19) : 4988 - 4991
  • [29] Construction of Diverse N-Heterocycles by Formal (3+3) Cycloaddition of Naphthol/Thionaphthol/Naphthylamine and 1,3,5-Triazinanes
    Liu, Xiang
    Wang, Yuhan
    Zheng, Huitao
    Huang, Junyan
    Su, Zhengquan
    Zhao, Limin
    Cao, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (01): : 75 - 85
  • [30] (3+3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans
    Chauhan, Sachin
    Debnath, Shubham
    Swamy, K. C. Kumara
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (24) : 5021 - 5032
12345