Synthesis of 2,3,4-trisubstituted pyrrole derivatives via [3+2] cyclization of activated methylene isocyanides with 4-(arylidene)-2-substituted oxazol-5(4H)-ones

被引:8
|
作者
Zhang, Jing [1 ,2 ]
Liu, Man [2 ]
Li, Chao [2 ]
Xu, Yan-Jun [1 ]
Dong, Lin [2 ]
机构
[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610066, Sichuan, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Peoples R China
关键词
ALPHA-ACIDIC ISOCYANIDES; REGIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; POLYSUBSTITUTED PYRROLES; SUBSTITUTED PYRROLES; CONGOCIDINE; ISOCYANOACETATES; ANNULATION; ALKYNES; YLIDES;
D O I
10.1039/c9qo01044k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient base-catalyzed [3 + 2] cyclization between isocyanides and 4-(arylidene)-2-substituted oxazol-5(4H)-ones has been successfully developed to form 2,3,4-trisubstituted and 2,2,3,4-tetrasubstituted pyrrole derivatives. This transition metal free reaction occurs at room temperature under environmentally friendly conditions, tolerating water and air.
引用
收藏
页码:420 / 424
页数:5
相关论文
共 50 条
  • [21] Synthesis of 1H-pyrano[4,3-b]benzofuran-1-one derivatives via photochemical cyclization of substituted 4H-furo[3,2-c]pyran-4-ones
    Milyutin, Constantine, V
    Lichitsky, Boris, V
    Melekhina, Valeriya G.
    Komogortsev, Andrey N.
    Fakhrutdinov, Artem N.
    Minyaev, Mikhail E.
    Krayushkin, Michail M.
    TETRAHEDRON LETTERS, 2020, 61 (44)
  • [22] A simple method for synthesis of 5-CF3 substituted dienamides via rearrangement of 2H-pyran derivatives
    Wang, Xiao-Wei
    Li, Peng
    Xiao, Hua
    Zhu, Shi-Zheng
    Zhao, Gang
    TETRAHEDRON, 2011, 67 (39) : 7618 - 7621
  • [23] Regioselective synthesis of 3-(aryloxyacetyl)-2,3-dihydrothieno-[2,3-b][1]benzothiopyran-4-ones via tandem cyclization
    Majumdar, KC
    Bandyopadhyay, A
    Ghosh, SK
    SYNTHETIC COMMUNICATIONS, 2004, 34 (12) : 2159 - 2167
  • [24] Metal-/solvent-free oxidative [4+2]/[3+2] annulation of 2-ethynylbenzaldehydes with arylalkenes: facile synthesis of benzo[a]fluoren-5-ones
    Wang, Cheng-Yong
    Yu, Jiang-Xi
    Liu, Bang
    Zhang, Fu-Xing
    Wang, Zhi-Qiang
    Hu, Qin-Yu
    Xu, Zhi-Feng
    Li, Jin-Heng
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (11): : 2939 - 2943
  • [25] Gold-catalyzed selective oxidation of 4-oxahepta-1,6-diynes to 2H-pyran-3(6H)-ones and chromen-3-(4H)-ones via β-gold vinyl cation intermediates
    Ji, Kegong
    Liu, Xiang
    Du, Bowen
    Yang, Fang
    Gao, Jinming
    CHEMICAL COMMUNICATIONS, 2015, 51 (51) : 10318 - 10321
  • [26] Synthesis of 3′,4′-Diaryl-4′H-spiro[indoline-3,5′-[1′,2′,4′]-oxadiazol]-2-ones via DMAP-catalyzed Domino Reactions and Their Antibacterial Activity
    Shi, Guanghao
    He, Xinwei
    Shang, Yongjia
    Xiang, Liwei
    Yang, Cheng
    Han, Guang
    Du, Bing
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (09) : 901 - 909
  • [27] Metal-Free [3+2] Tandem Cyclization Synthesis of Unique 11H-Pyrido[3,2:4,5]Pyrrolo[3,2-b]Indolizine from 7-Azaindoles and Pyridotriazoles
    Zhang, Guo-Tai
    Zhang, Jing
    Xu, Yan-Jun
    Dong, Lin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4197 - 4201
  • [28] Electrophilic cyclization of 3-alkynyl-4-chalcogen-2-H-chromenes: synthesis of 3-halo-chalcogenophene[3,2-c]chromene derivatives
    Speranca, Adriane
    Godoi, Benhur
    Costa, Michael Daniel
    Menezes, Paulo Henrique
    Zeni, Gilson
    TETRAHEDRON LETTERS, 2011, 52 (03) : 388 - 391
  • [29] Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones
    Nori, Valeria
    Arcadi, Antonio
    Carlone, Armando
    Marinelli, Fabio
    Chiarini, Marco
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 1084 - 1091
  • [30] Enantioselective Synthesis of Spiropyrazolone-Fused Cyclopenta[c]chromen-4-ones Bearing Five Contiguous Stereocenters via (3+2) Cycloaddition
    Khairnar, Pankaj, V
    Su, Yin-Hsiang
    Edukondalu, Athukuri
    Lin, Wenwei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17): : 12326 - 12335