Metal-free ring opening of 5-amino-1,4-diaryl-1H-pyrazoles: A facile access to 2-aryl-3-arylazoacrylonitriles

被引:4
作者
Chatterjee, Arpita [1 ]
Radhakrishnan, Divya [1 ]
Bandyopadhyay, Debashruti [1 ]
Kanchithalaivan, Selvaraj [1 ]
Peruncheralathan, Saravanan [1 ]
机构
[1] Natl Inst Sci Educ & Res NISER, Sch Chem Sci, Bhubaneswar, India
关键词
H BOND AMINATION; CONJUGATED AZOALKENES; INHIBITORS; 5-AMINOPYRAZOLES; IDENTIFICATION; CARBAZOLE; ARENES;
D O I
10.1002/jhet.4439
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various 2-aryl-3-arylazoacrylonitriles are synthesized while attempting the intramolecular N-arylation of 5-aminopyrazoles, using the hypervalent iodine reagent. The synthesis involves phenyl iodine diacetate-assisted ring opening of 5-aminopyrazoles at room temperature. A plausible mechanism for the formation of azoalkenes is proposed.
引用
收藏
页码:1016 / 1024
页数:9
相关论文
共 48 条
  • [21] Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components
    Li, Bi-He
    Tian, Shi-Liang
    Fang, Zhao
    Shi, Zhang-Jie
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) : 1115 - 1118
  • [22] Recent Advances in the Chemistry of Conjugated Nitrosoalkenes and Azoalkenes
    Lopes, Susana M. M.
    Cardoso, Ana L.
    Lemos, Americo
    Pinho e Melo, Teresa M. V. D.
    [J]. CHEMICAL REVIEWS, 2018, 118 (23) : 11324 - 11352
  • [23] Oxidative conversion of N-substituted 3-aminopyrazoles to azopyrazoles using electrogenerated NaOCl as the mediator
    Lyalin, Boris V.
    Sigacheva, Vera L.
    Kokorekin, Vladimir A.
    Petrosyan, Vladimir A.
    [J]. ARKIVOC, 2017, : 55 - 62
  • [24] An Organic Intermolecular Dehydrogenative Annulation Reaction
    Maiti, Saikat
    Achar, Tapas Kumar
    Mal, Prasenjit
    [J]. ORGANIC LETTERS, 2017, 19 (08) : 2006 - 2009
  • [25] Hypervalent Iodine(III) in Direct Oxidative Amination of Arenes with Heteroaromatic Amines
    Manna, Srimanta
    Serebrennikova, Polina O.
    Utepova, Irina A.
    Antonchick, Andrey P.
    Chupakhin, Oleg N.
    [J]. ORGANIC LETTERS, 2015, 17 (18) : 4588 - 4591
  • [26] 1,2-Diaza-1,3-diene-Based Multicomponent Reactions in Sequential Protocols to Synthesize Arylamino-5-hydrazonothiophene-3-carboxylates
    Mari, Giacomo
    De Crescentini, Lucia
    Favi, Gianfranco
    Santeusanio, Stefania
    Mantellini, Fabio
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (46) : 6548 - 6556
  • [27] Enantioselective Dearomatization of Indoles by an Azoalkene-Enabled (3+2) Reaction: Access to Pyrroloindolines
    Mei, Guang-Jian
    Tang, Xiwen
    Tasdan, Yildiz
    Lu, Yixin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (02) : 648 - 652
  • [28] Palladium-Catalyzed Amidation of Unactivated C(sp3)-H Bonds: from Anilines to Indolines
    Neumann, Julia J.
    Rakshit, Souvik
    Droege, Thomas
    Glorius, Frank
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6892 - 6895
  • [29] Oxidative Ring-Opening of 1H-Pyrazol-5-amines and Its Application in Constructing Pyrazolo-Pyrrolo-Pyrazine Scaffolds by Domino Cyclization
    Pan, Lei
    Jin, Feng
    Fu, Rui
    Gao, Ke
    Zhou, Shaofang
    Bao, Xiaoguang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (19) : 2956 - 2961
  • [30] PALLADIUM-CATALYZED FORMATION OF CARBON-NITROGEN BONDS - REACTION INTERMEDIATES AND CATALYST IMPROVEMENTS IN THE HETERO CROSS-COUPLING OF ARYL HALIDES AND TIN AMIDES
    PAUL, F
    PATT, J
    HARTWIG, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) : 5969 - 5970