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
  • [21] Regio- and Stereoselective Hydrophosphorylation of Ynamides for the Synthesis of β-Aminovinylphosphine Oxides
    Huang, Hai
    Zhu, Hongjun
    Kang, Jun Yong
    ORGANIC LETTERS, 2018, 20 (09) : 2778 - 2781
  • [22] Regio- and stereoselective synthesis of α,β-dehydro-β-amino esters
    Li, Dafeng
    Li, Jian
    Jia, Xueshun
    JOURNAL OF CHEMICAL RESEARCH, 2008, (08) : 434 - 436
  • [23] Regio- and Stereoselective Synthesis of Multisubstituted Vinylsilanes via Zirconacycles
    Nishihara, Yasushi
    Saito, Daisuke
    Tanemura, Kenki
    Noyori, Shintaro
    Takagi, Kentaro
    ORGANIC LETTERS, 2009, 11 (16) : 3546 - 3549
  • [24] Regio- and stereoselective synthesis of LNA guanine nucleosides.
    Rosenhohm, C
    Pedersen, DS
    Koch, T
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U173 - U173
  • [25] Regio- and stereoselective synthesis of α-hydroxy-β-azido tetrazoles
    Quinodoz, Pierre
    Lo, Cheikh
    Kletskii, Mikhail
    Burov, Oleg
    Marrot, Jerome
    Couty, Francois
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (05): : 492 - 496
  • [26] Regio- and stereoselective synthesis of 4′-thiaspiroacetals from carbohydrates
    Bartolozzi, A
    Capozzi, G
    Falciani, C
    Menichetti, S
    Nativi, C
    Bacialli, AP
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17): : 6490 - 6494
  • [27] Regio- and stereoselective synthesis of fluoroalkadienes using β-fluoroalkenyliodonium salt
    Yoshida, M
    Nagahara, D
    Fukuhara, T
    Yoneda, N
    Hara, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (18): : 2283 - 2288
  • [28] A regio- and stereoselective synthesis of beta-amino alcohols
    Fu, XL
    Wu, SH
    SYNTHETIC COMMUNICATIONS, 1997, 27 (10) : 1677 - 1683
  • [29] Regio- and stereoselective synthesis of 1,4-dienes
    Oishi, Shigeki
    Hatano, Keisuke
    Tsubouchi, Akira
    Takeda, Takeshi
    CHEMICAL COMMUNICATIONS, 2011, 47 (42) : 11639 - 11640
  • [30] Regio- and stereoselective synthesis of (Z)-vinylgermanes by hydrogermylation of alkynes
    David-Quillot, Frank
    Thiery, Valerie
    Abarbri, Mohamed
    Thibonnet, Jerome
    Besson, Thierry
    Duchene, Alain
    MAIN GROUP METAL CHEMISTRY, 2007, 30 (05) : 235 - 244