Direct Access for the Regio- and Stereoselective Synthesis of N-Alkenylpyrazoles and Chromenopyrazoles

被引：14
|
作者：
Kurma, Siva Hariprasad [1 ,2 ]
Sridhar, Balasubramanian [3 ]
Bhimapaka, China Raju [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
[3] CSIR Indian Inst Chem Technol, Dept Analyt & Struct Chem, Hyderabad 500007, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 03期
关键词：
ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; FACILE SYNTHESIS; PYRAZOLES; HYDRAZONES; ALKYNES; TOSYLHYDRAZONES; DERIVATIVES; HYDRAZIDES; COMPLEXES;
D O I：
10.1021/acs.joc.0c02421
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly regio- and stereoselective method was developed for the preparation of N-alkenylpyrazoles and chromenopyrazoles by the reaction of N-tosylhydrazones and salicyl N-tosylhydrazones with alkynes under neat conditions in the presence of La(OTf)(3). The present study was found to be efficient and convenient for direct access to N-alkenylpyrazoles and chromenopyrazoles through C-C, C-N, and C-O bond forming reactions. Structure assignment of N-alkenylpyrazole compound 5c was confirmed by X-ray analysis.
引用
收藏
页码：2271 / 2282
页数：12
相关论文
共 50 条
  • [11] A double regio- and stereoselective glycosylation strategy for the synthesis of N-glycans
    Unverzagt, Carlo
    Eller, Steffen
    Mezzato, Stefano
    Schuberth, Ralf
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (04) : 1304 - 1311
  • [12] Theoretical analysis of the regio- and stereoselective synthesis of spiroisoxazolines
    Acharjee, Nivedita
    JOURNAL OF MOLECULAR MODELING, 2020, 26 (06)
  • [13] Regio- and Stereoselective Synthesis of β-Methylthio Vinyl Triflates
    Tang, Meizhong
    Wei, Yongjiao
    Huang, Shenlin
    Xie, Lan-Gui
    ORGANIC LETTERS, 2022, : 7026 - 7030
  • [14] Regio- and stereoselective synthesis of glycosyl phosphinic acids
    Tzokov, SB
    Devedjiev, IT
    Petkov, DD
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01): : 12 - 13
  • [15] Regio- and Stereoselective Multisubstituted Enol Ester Synthesis
    Okamoto, Noriko
    Miwa, Yoshihisa
    Minami, Hideki
    Takeda, Kei
    Yanada, Reiko
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 9133 - 9138
  • [16] Theoretical analysis of the regio- and stereoselective synthesis of spiroisoxazolines
    Nivedita Acharjee
    Journal of Molecular Modeling, 2020, 26
  • [17] Regio- and Stereoselective Switchable Synthesis of (E)- and (Z)-N-Carbonylvinylated Pyrazoles
    Zhang, Xue
    Zhang, Zheyu
    Yu, Haifeng
    Che, Guangbo
    MOLECULES, 2023, 28 (11):
  • [18] Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
    Chen, Junting
    Li, Jiakun
    Plutschack, Matthew B.
    Berger, Florian
    Ritter, Tobias
    Advanced Materials, 2020, 132 (14) : 5665 - 5669
  • [19] Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
    Chen, Junting
    Li, Jiakun
    Plutschack, Matthew B.
    Berger, Florian
    Ritter, Tobias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5616 - 5620
  • [20] Synthesis of More Highly Oxidized Alkyl Citrates via Direct Regio- and Stereoselective Oxidation
    Rossouw, Nikolai P.
    Chen, Zongjia
    White, Jonathan M.
    Rizzacasa, Mark A.
    ORGANIC LETTERS, 2023, 25 (44) : 8010 - 8015
12345