I- catalyzed cascade annulation of 2-(pyridin-2-yl)acetate derivatives with N , N- dimethylenamine 2 ketones: Site-selective synthesis of functionalized indolizines

被引:0
|
作者
Li, Yuan -Da [1 ]
Zhang, Wei-Min [1 ]
Zhao, Ke-Hua [1 ]
Zhang, Cong-Hai [1 ]
Yan, Sheng-Jiao [1 ]
机构
[1] Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resources, Minist Educ, Kunming 650091, Peoples R China
关键词
I2-Catalysis; Cascade annulation; Indolizines; NN-Dimethyl-enamine ketones; ONE-POT SYNTHESIS; METAL-FREE SYNTHESIS; BIOLOGICAL EVALUATION; FLUORESCENT-PROBES; CYCLIZATION; ALKYNES; DESIGN; ENAMINONES; IMIDAZOLE; HYBRIDS;
D O I
10.1016/j.tet.2024.134015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel synthesis method was developed for developing functionalized indolizines. In this reaction, 2-(pyridin-2yl)acetate derivatives and N , N -dimethylenamine ketones were used as substrates. All these processes were enabled by heating a mixture of starting materials in toluene and in the presence of I 2 under air. Cascade reaction resulted in the formation of two bonds and cleavage of one bond in one pot. Consequently, a number of functionalized indolizines were produced via a cascade reaction. This protocol can be used to synthesize functionalized unsymmetrical 2,4-diarylpyridines. Moreover, it is suitable for combinatorial and parallel syntheses of indolizines derivatives in a one -pot reaction and it is not a tedious multi -step reaction.
引用
收藏
页数:9
相关论文
共 50 条
  • [11] An environmentally benign cascade reaction of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective synthesis of quinolizines and quinolizinium salts in water
    Chen, Li
    Huang, Rong
    Li, Kun
    Yun, Xing-Han
    Yang, Chang-Long
    Yan, Sheng-Jiao
    GREEN CHEMISTRY, 2020, 22 (20) : 6943 - 6953
  • [12] An efficient and convenient one-pot multicomponent synthesis of novel pyrimidine derivatives: N-(4-aryl-6-(pyridin-2-yl)pyrimidin-2-yl)cyanamides
    Rong, Liangce
    Wei, Xianyong
    Tao, Shimin
    Lu, Yao
    Xie, Ruilun
    Zhou, Jun
    Zong, Zhimin
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (04) : 1907 - 1916
  • [13] Direct Oxidative Cleavage of Multiple Csp3-H Bonds and a C-C Bond in 2-(Pyridin-2-yl)acetate Derivatives: Formal [3+1+1] Synthesis of 3-(Pyridin-2-yl)indolizine Skeletons
    Wu, Xia
    Zhao, Peng
    Geng, Xiao
    Zhang, Jingjing
    Gong, Xingxing
    Wu, Yan-dong
    Wu, An-xin
    ORGANIC LETTERS, 2017, 19 (12) : 3319 - 3322
  • [14] Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
    Liu, Yanpeng
    Lu, Lixue
    Zhou, Haipin
    Xu, Feijie
    Ma, Cong
    Huang, Zhangjian
    Xu, Jinyi
    Xu, Shengtao
    RSC ADVANCES, 2019, 9 (59) : 34671 - 34676
  • [15] Organophotoredox-Catalyzed Cascade Radical Annulation of 2-(Allyloxy)arylaldehydes with N-(acyloxy)phthalimides: Towards Alkylated Chroman-4-one Derivatives
    Das, Sanju
    Parida, Sushanta Kumar
    Mandal, Tanumoy
    Sing, Laxmikanta
    De Sarkar, Suman
    Murarka, Sandip
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (05) : 568 - 572
  • [16] Hypervalent Iodine Promoted Regioselective Oxidative C-H Functionalization: Synthesis of N-(Pyridin-2-yl)benzo[d]thiazol-2-amines
    Mariappan, Arumugam
    Rajaguru, Kandasamy
    Roja, Somi Santharam
    Muthusubramanian, Shanmugam
    Bhuvanesh, Nattamai
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (02) : 302 - 307
  • [17] Synthesis of 2-[4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio]-N-(thiazole-2-yl)acetamide derivatives and their anticancer activities
    Duran, Murat
    Demirayak, Seref
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (09) : 4110 - 4124
  • [18] Palladium Catalyzed Tricyclohexylphosphine Ligand Associated Synthesis of N-(2-(pyridine-4-yl)-1H-pyrrolo[3,2-c]-pyridin-6-yl-(substituted)-sulfonamide Derivatives as Antiproliferative Agents
    Pawar, Chandrakant D.
    Sarkate, Aniket P.
    Karnik, Kshipra S.
    Shinde, Devanand B.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (07) : 1695 - 1701
  • [19] N-(4-(4-Chlorophenyl)Thiazol-2-yl)-2-(2-Phenylacetamido) Acetamide Derivatives as Potential Anticancer Agents: Synthesis and Cytotoxicity Evaluation
    Aliabadi, Ali Reza
    Farani, Ahmad Mohammadi
    Nikray, Semko
    Hosseini, Amin
    Foroumadi, Ali Reza
    Aliabadi, Amin
    IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2024, 43 (06): : 2188 - 2202
  • [20] Synthesis, molecular docking, and pharmacological evaluation of N-(2-(3,5-dimethoxyphenyl)benzoxazole-5-yl)benzamide derivatives as selective COX-2 inhibitors and anti-inflammatory agents
    Kaur, Avneet
    Pathak, Dharam P.
    Sharma, Vidushi
    Wakode, Sharad
    ARCHIV DER PHARMAZIE, 2018, 351 (06)