Base-promoted ring-closing carbonyl-allene metathesis for the synthesis of 2,4-disubstituted pyrroles

被引：28
作者：
Cheng, Guolin [1 ]
Lv, Weiwei [1 ]
Xue, Lulu [1 ]
机构：
[1] Huaqiao Univ, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China
来源：
GREEN CHEMISTRY | 2018年 / 20卷 / 19期
关键词：
PROPARGYLIC BETA-ENAMINONES; OLEFIN METATHESIS; FACILE SYNTHESIS; 3-COMPONENT SYNTHESIS; AROMATIC-COMPOUNDS; CASCADE REACTION; ALKYNYL IMINES; CYCLIZATION; ESTERS; COPPER;
D O I：
10.1039/c8gc01675e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A base-promoted ring-closing carbonyl-allene metathesis reaction of N-allenyl beta-enaminones (generated in situ from N-propargyl beta-enaminones) gives 2,4-disubstituted pyrroles with cleavage of the C(sp)-C(sp(3)) bond. This transition metal-free procedure generates 1 equiv. of acetic acid as the sole byproduct. A preliminary mechanistic study supports a stepwise [2 + 2] cycloaddition/retro [2 + 2] reaction pathway.
引用
收藏
页码：4414 / 4417
页数：5
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  • [1] N-Propargylic β-enaminocarbonyls: powerful and versatile building blocks in organic synthesis
    Arshadi, Sattar
    Vessally, Esmail
    Edjlali, Ladan
    Ghorbani-Kalhor, Ebrahim
    Hosseinzadeh-Khanmiri, Rahim
    [J]. RSC ADVANCES, 2017, 7 (22) : 13198 - 13211
  • [2] Cyclocondensation of α-Aminonitriles and Enones: A Short Access to 3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles
    Bergner, Ines
    Wiebe, Christine
    Meyer, Nino
    Opatz, Till
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) : 8243 - 8253
  • [3] Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics
    Bhardwaj, Varun
    Gumber, Divya
    Abbot, Vikrant
    Dhiman, Saurabh
    Sharma, Poonam
    [J]. RSC ADVANCES, 2015, 5 (20): : 15233 - 15266
  • [4] N-propargylic β-enaminones:: Common intermediates for the synthesis of polysubstituted pyrroles and pyridines
    Cacchi, Sandro
    Fabrizi, Giancarlo
    Filisti, Eleonora
    [J]. ORGANIC LETTERS, 2008, 10 (13) : 2629 - 2632
  • [5] Bronsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host
    Catti, Lorenzo
    Tiefenbacher, Konrad
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (44) : 14589 - 14592
  • [6] 2,4-vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts
    Chen, Feng
    Shen, Tao
    Cui, Yuxin
    Jiao, Ning
    [J]. ORGANIC LETTERS, 2012, 14 (18) : 4926 - 4929
  • [7] Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C-C bond cleavage
    Cheng, Guolin
    Lv, Weiwei
    Kuai, Changsheng
    Wen, Si
    Xiao, Shangyun
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (14) : 1726 - 1729
  • [8] Transition-Metal-Free Cascade Approach toward 2-Alkoxy/2-Sulfenylpyridines and Dihydrofuro[2,3-b]pyridines by Trapping In Situ Generated 1,4-Oxazepine
    Cheng, Guolin
    Xue, Lulu
    Weng, Yunxiang
    Cui, Xiuling
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18) : 9515 - 9524
  • [9] Base-Promoted N-Pyridylation of Heteroarenes Using N-Propargyl Enaminones as Equivalents of Pyridine Scaffolds
    Cheng, Guolin
    Weng, Yunxiang
    Yang, Xifa
    Cui, Xiuling
    [J]. ORGANIC LETTERS, 2015, 17 (15) : 3790 - 3793
  • [10] A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Cheng, Guolin
    Zeng, Xiaobao
    Shen, Jinhai
    Wang, Xuesong
    Cui, Xiuling
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13265 - 13268
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