Facile synthesis of 2-substituted benzofurans by intermolecular [3+2] cycloaddition of benzoquinone and vinyl azides under air

被引：0
|
作者：
Sun, Pengfei [2 ]
Yu, Xin [1 ]
Wei, Fang [1 ]
机构：
[1] Jiangxi Sci & Technol Normal Univ, Inst Organ Chem, Jiangxi Prov Key Lab Organ Funct Mol, Nanchang 330013, Peoples R China
[2] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
来源：
TETRAHEDRON | 2024年 / 167卷
关键词：
Vinyl azides; Benzofurans; 3+2] cycloaddition; ONE-POT SYNTHESIS; DONOR-ACCEPTOR CYCLOPROPANES; CYCLIZATION; PHENOLS; 2-HALOPHENOLS; HETEROCYCLES; DERIVATIVES; INDOLES; ALKYNES;
D O I：
10.1016/j.tet.2024.134277
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of a transition-metal-catalyzed [3 + 2] cycloaddition for one-pot synthesis of 2-substituted benzofurans from vinyl azides and benzoquinone is reported. This reaction could be carried out under mild conditions without the need to isolate air, giving desired products in good to excellent yields.
引用
收藏
页数：7
相关论文
共 50 条
  • [21] Synthesis of Substituted Tetrahydrocyclobuta[b]benzofurans by Palladium-Catalyzed Substitution/[2+2] Cycloaddition of Propargylic Carbonates with 2-Vinylphenols
    Yoshida, Masahiro
    Ohno, Shoko
    Namba, Kosuke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) : 13597 - 13600
  • [22] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition
    Davies, Paul W.
    Cremonesi, Alex
    Dumitrescu, Lidia
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) : 8931 - 8935
  • [23] Silver-Catalyzed [3+2] Cycloaddition for the Diastereoselective Synthesis of anti-3-Substituted Hydroindolin-2-Imines
    Yang, Zhongtao
    Luo, Xiai
    Zhang, Zhipeng
    Luo, Xiaoling
    Zheng, Jia
    Luo, Hui
    Yang, Weiguang
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) : 4433 - 4439
  • [24] Synthesis of trifluoromethylated pyrazolidines by [3+2] cycloaddition
    Peng, Xiansha
    Huang, Danfeng
    Wang, Ke-Hu
    Wang, Yalin
    Wang, Juanjuan
    Su, Yingpeng
    Hu, Yulai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (29) : 6214 - 6222
  • [25] Multicomponent Methanolysis Reaction for the Synthesis Pyrrole and Pyrolizine Derivatives via Intermolecular (3+2) Cycloaddition
    Shirsat, Prashishkumar K.
    Khomane, Navnath B.
    Mali, Prakash R.
    Maddi, Raghavender Reddy
    Nanubolu, Jagadeesh Babu
    Meshram, Harshadas M.
    CHEMISTRYSELECT, 2017, 2 (34): : 11218 - 11222
  • [26] Synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed intermolecular coupling of 2-fluoroallylic acetates with phenols
    Udagawa, Takumi
    Kogawa, Masaki
    Tsuchi, Yukiko
    Watanabe, Hirotaka
    Yamamoto, Mitsuaki
    Kawatsura, Motoi
    TETRAHEDRON LETTERS, 2017, 58 (03) : 227 - 230
  • [27] Photocatalytic Synthesis of Dihydrobenzofurans by Oxidative [3+2] Cycloaddition of Phenols
    Blum, Travis R.
    Zhu, Ye
    Nordeen, Sarah A.
    Yoon, Tehshik P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) : 11056 - 11059
  • [28] Modification of nucleic acids using [3+2]-dipolar cycloaddition of azides and alkynes
    Ustinov, A. V.
    Stepanova, I. A.
    Dubnyakova, V. V.
    Zatsepin, T. S.
    Nozhevnikova, E. V.
    Korshun, V. A.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2010, 36 (04) : 401 - 445
  • [29] Et2Zn-Mediated Radical (3+2) Cycloaddition of Vinyl Azides with Ethyl Iododifluoroacetate to Access 3,3-Difluoro-γ-lactams
    Zhang, Yifei
    Jiang, Bin
    Liu, Peijun
    Liu, Xiaozu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (20): : 14634 - 14639
  • [30] Synthesis of indol-3-yl-benzofurans and carbazoles via Cu(OTf)2-catalyzed [3+2] and [4+2] cycloaddition
    Chauhan, Amar Nath Singh
    Vini, Vikrant
    Kumar, Akhilesh
    Erande, Rohan D.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (33) : 6690 - 6694
12345