Rhodium-Catalyzed [3+2]-Cycloaddition of in-situ Generated Nitrile Ylides with Nitrosoarenes

被引：1
作者：
Yao, Wei-Zhong [1 ]
Cai, Bao-Gui [1 ]
Xuan, Jun [1 ,2 ]
机构：
[1] Anhui Univ, Coll Chem & Chem Engn, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Funct, Hefei 230601, Anhui, Peoples R China
[2] Anhui Univ, Key Lab Struct & Funct Regulat Hybrid Mat, Minist Educ, Hefei 230601, Anhui, Peoples R China
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2024年 / 19卷 / 03期
基金：
中国国家自然科学基金;
关键词：
nitrile ylides; nitrosoarenes; 1,2,4-oxadiazoles; carbene chemistry; rhodium catalysis; SOLID-PHASE SYNTHESIS; CYCLOADDITION; 2-NITROSOPYRIDINE; DERIVATIVES; IMIDAZOLES; AMIDINES; OXAZOLES; PYRROLES;
D O I：
10.1002/asia.202301053
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein we report the rhodium-catalyzed one-pot three-component reaction of diazo compounds, nitriles, and nitrosoarenes to construct 2,5-dihydro-1,2,4-oxadiazole derivatives. Mechanistic studies indicate that the transformation may proceed through the formation of nitrile ylides intermediates, which then undergo [3+2]-cycloaddition with nitrosoarenes. The strategy exhibits several synthetic advantages, including operational simplicity, good functional group tolerance, and scalability.
引用
收藏
页数：4
相关论文
共 50 条
  • [1] Current Parallel Solid-Phase Synthesis of Drug-like Oxadiazole and Thiadiazole Derivatives for Combinatorial Chemistry
    Abdildinova, Aizhan
    Gong, Young-Dae
    [J]. ACS COMBINATORIAL SCIENCE, 2018, 20 (06) : 309 - 329
  • [2] CpRu-Catalyzed O-H Insertion and Condensation Reactions of α-Diazocarbonyl Compounds
    Austeri, Martina
    Rix, Diane
    Zeghida, Walid
    Lacour, Jerome
    [J]. ORGANIC LETTERS, 2011, 13 (06) : 1394 - 1397
  • [3] Copper-exchanged bentonite: a reusable catalysis for the formation of alkoxycarbonyl nitrile ylides under microwave irradiation
    Bendedouche, Choukri Kamel
    Benhaoua, Hadj
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2012, (03) : 149 - 151
  • [4] Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery
    Biernacki, Karol
    Dasko, Mateusz
    Ciupak, Olga
    Kubinski, Konrad
    Rachon, Janusz
    Demkowicz, Sebastian
    [J]. PHARMACEUTICALS, 2020, 13 (06)
  • [5] A New Pyrrole Synthesis via Silver(I)-Catalyzed Cycloaddition of Vinylogous Diazoester and Nitrile
    Billedeau, Roland J.
    Klein, Klara R.
    Kaplan, Daniel
    Lou, Yan
    [J]. ORGANIC LETTERS, 2013, 15 (07) : 1421 - 1423
  • [6] Oxadiazoles in Medicinal Chemistry
    Bostrom, Jonas
    Hogner, Anders
    Llinas, Antonio
    Wellner, Eric
    Plowright, Alleyn T.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (05) : 1817 - 1830
  • [7] The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition
    Breugst, Martin
    Reissig, Hans-Ulrich
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (30) : 12293 - 12307
  • [8] Copper-triggered three-component reaction of CF3CHN2, nitriles, and aldehydes: highly diastereoselective synthesis of CF3-substituted oxazolines and vicinal amino alcohols
    Cai, Ai-Jie
    Zheng, Yan
    Ma, Jun-An
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (43) : 8946 - 8949
  • [9] Photochemical multicomponent transformation of acceptor-only diazoalkanes by merging their cycloaddition and carbene reactivities
    Cai, Bao-Gui
    Xu, Guo-Yong
    Xuan, Jun
    [J]. CHINESE CHEMICAL LETTERS, 2023, 34 (09)
  • [10] Copper-catalyzed 2,3-dihydro-1,2,4-triazoles synthesis through [3+2]-cycloaddition of nitrile ylides with azodicarboxylates
    Cai, Bao-Gui
    Li, Qian
    Xuan, Jun
    [J]. GREEN SYNTHESIS AND CATALYSIS, 2024, 5 (03): : 191 - 194
12345