Facile three-component reactions for the synthesis of N-unsubstituted 1H-pyrrol-3(2H)-ones and base induced divergent N-H and C-C bond derivatizations

被引：4
|
作者：
Cao, Jia-xuan [1 ]
Hua, Wei-jie [1 ]
Jiang, Jun-cen [1 ]
Chen, Min [1 ]
Sha, Qiang [1 ]
机构：
[1] Nanjing Agr Univ, Coll Sci, Dept Chem, Jiangsu Key Lab Pesticide Sci, 1 Weigang Rd, Nanjing 210095, Peoples R China
来源：
TETRAHEDRON | 2022年 / 125卷
关键词：
Heterocycles; Multicomponent reactions; Cascade reactions; 2; 3-Diketoesters; Rearrangement reactions; METAL-FREE SYNTHESIS; CYCLIZATION; CHEMISTRY; DERIVATIVES; CASCADE; PYRROLIN-4-ONES; ALKALOIDS; MIGRATION; EFFICIENT; DESIGN;
D O I：
10.1016/j.tet.2022.133038
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we present a facile three-component reaction of 2,3-diketoesters, ammonium acetate and ke-tones that yielded a variety of N-unsubstituted 1H-pyrrol-3(2H)-ones in moderate to good yields. Sub-sequently, base-induced divergent N-H and C-C bond derivatizations of N-unsubstituted 1H-pyrrol-3(2H)-ones were revealed. By using NaH as the base, N-alkylation, acylation and sulfonylation occur smoothly. When NaOH is used, C-C(1/4O) cleavage occurs and further Michael addition reaction happens, resulting in the installation of an alkyl chain at the 2-position of the 1H-pyrrol-3(2H)-one skeleton.(c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数：6
相关论文
共 50 条
  • [31] A facile eco-friendly three-component protocol for the regio- and stereoselective synthesis of functionalized trans-dihydrofuro[3,2-c]-quinolin-4(2H)-ones
    Indumathi, Sethuraman
    Perumal, Subbu
    Anbananthan, Natarajan
    GREEN CHEMISTRY, 2012, 14 (12) : 3361 - 3367
  • [32] RhIII-Catalyzed C-H Allylation of Amides and Domino Cycling Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones with N-Bromosuccinimide
    Dai, Huimin
    Yu, Chao
    Lu, Changsheng
    Yan, Hong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (07) : 1255 - 1259
  • [33] One-Pot Three-Component Synthesis of Tetrasubstituted N-H Pyrroles from Secondary Propargylic Alcohols, 1,3-Dicarbonyl Compounds and tert-Butyl Carbamate
    Cadierno, Victorio
    Gimeno, Jose
    Nebra, Noel
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (01) : 233 - 236
  • [34] Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: facile synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols
    Li, Ting
    Wang, Zhen
    Zhang, Mingliang
    Zhang, Hui-Jun
    Wen, Ting-Bin
    CHEMICAL COMMUNICATIONS, 2015, 51 (31) : 6777 - 6780
  • [35] Octyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate: complex sheets built from N-H•••N, C-H•••N and C-H•••O hydrogen bonds
    Cortes, Edwar
    Abonia, Rodrigo
    Cobo, Justo
    Glidewell, Christopher
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2014, 70 : 617 - +
  • [36] Rh-Catalyzed C-C/C-N bond formation via C-H activation: synthesis of 2H-indazol-2-yl-benzo[a]carbazoles
    Kumar, Sundaravel Vivek
    Banerjee, Sonbidya
    Punniyamurthy, Tharmalingam
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (23): : 3885 - 3890
  • [37] Copper-Catalyzed Domino Synthesis of 2-Imino-1H-imidazol-5(2H)-ones and Quinoxalines Involving C-C Bond Cleavage with a 1,3-Dicarbonyl Unit as a Leaving Group
    Yang, Yan
    Ni, Fan
    Shu, Wen-Ming
    Wu, An-Xin
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (37) : 11776 - 11782
  • [38] Iridium mediated N-H and C-H bond activation of N-(aryl)pyrrole-2-aldimines. Synthesis, structure and, spectral and electrochemical properties
    Paul, Piyali
    Bhattacharya, Samaresh
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 713 : 72 - 79
  • [39] Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones
    Bansode, Ajay H.
    Suryavanshi, Gurunath
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (05) : 1390 - 1400
  • [40] An Effient Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives via Isocyanide Insertion into the N-H Bond of 2-(1H-pyrrol-1-yl)anilines
    Luo, Liangliang
    Xiong, Tong
    Zhou, Liyan
    Zeng, Qin
    Xiao, You-Cai
    Chen, Fen-Er
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (11) : 2927 - 2931
12345