Rhodium-Catalyzed Addition Cyclization of Hydrazines with Alkynes: Pyrazole Synthesis via Unexpected C-N Bond Cleavage

被引:63
|
作者
Li, Deng Yuan
Mao, Xiao Feng
Chen, Hao Jie
Chen, Guo Rong
Liu, Pei Nian [1 ]
机构
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China
关键词
REGIOSELECTIVE SYNTHESIS; INTRAMOLECULAR CARBOALKOXYLATION; DECARBONYLATIVE ADDITION; GOLD; PLATINUM; NICKEL; CARBOSTANNYLATION; CYCLOADDITION; ARYNES; CARBOTHIOLATION;
D O I
10.1021/ol501402p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium-catalyzed addition-cyclization of hydrazines with alkynes has been achieved to afford highly substituted pyrazoles under mild conditions. The cascade reaction involves two transformations: addition of the C-N bond of hydrazines to alkynes via unexpected C-N bond cleavage and intramolecular dehydration cyclization.
引用
收藏
页码:3476 / 3479
页数:4
相关论文
共 50 条
  • [1] Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage
    Mochida, Satoshi
    Umeda, Nobuyoshi
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMISTRY LETTERS, 2010, 39 (07) : 744 - 746
  • [2] Rhodium-Catalyzed Synthesis of 2-Methylindoles via C-N Bond Cleavage of N-Allylbenzimidazole
    Biswal, Pragati
    Nanda, Tanmayee
    Prusty, Namrata
    Mohanty, Smruti Ranjan
    Ravikumar, Ponneri C.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 7988 - 7997
  • [3] Synthesis of Siloles via Rhodium-Catalyzed Cyclization of Alkynes and Diynes with Hexamethyldisilane
    Matsuda, Takanori
    Suda, Yuya
    Fujisaki, Yosuke
    SYNLETT, 2011, (06) : 813 - 816
  • [4] Rhodium-catalyzed rapid synthesis of substituted phenols from cyclobutenones and alkynes or alkenes via C-C bond cleavage
    Kondo, Teruyuki
    Niimi, Masatsugu
    Nomura, Masato
    Wada, Kenji
    Mitsudo, Take-aki
    TETRAHEDRON LETTERS, 2007, 48 (16) : 2837 - 2839
  • [5] Rhodium-catalyzed intramolecular carbosilylation of alkynes via C(sp3)-Si bond cleavage
    Yang, Qi
    Liu, Liang
    Chi, Yue
    Hao, Wei
    Zhang, Wen-Xiong
    Xi, Zhenfeng
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (05): : 860 - 863
  • [6] Rhodium-catalyzed alkenylation of allylbenzenes via C-C bond cleavage
    Kakiuchi, Fumitoshi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [7] Palladium-Catalyzed Hydroaminocarbonylation of Alkynes with Tertiary Amines via C-N Bond Cleavage
    Gao, Bao
    Huang, Hanmin
    ORGANIC LETTERS, 2017, 19 (22) : 6260 - 6263
  • [8] Rhodium-Catalyzed Coupling Reaction of Salicyl Aldehydes with Alkynes via Cleavage of the Aldehyde C-H Bond
    Kokubo, K.
    Matsumasa, K.
    Miura, M.
    Nomura, M.
    Journal of Organic Chemistry, 62 (14):
  • [9] Rhodium-catalyzed coupling reaction of salicyl aldehydes with alkynes via cleavage of the aldehyde C-H bond
    Kokubo, K
    Matsumasa, K
    Miura, M
    Nomura, M
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14): : 4564 - 4565
  • [10] Synthesis of Phenanthridines via a Rhodium-Catalyzed C-C Bond Cleavage Reaction of Biphenylene with Nitriles
    Korotvicka, Ales
    Frejka, David
    Hampejsova, Zuzana
    Cisarova, Ivana
    Kotora, Martin
    SYNTHESIS-STUTTGART, 2016, 48 (07): : 987 - 996