Efficient synthesis of spiro diheterocycles via multi-component dicyclization reaction

被引：4
作者：
Wang, Lingfeng [1 ,2 ,3 ]
Zhao, Peng [2 ,3 ]
Li, Song [2 ,3 ]
Ma, Yongmin [2 ,3 ]
Zhang, Pengfei [1 ]
Xu, Weiming [1 ]
机构：
[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Peoples R China
[2] Taizhou Univ, Inst Adv Studies, Jiaojiang 318000, Zhejiang, Peoples R China
[3] Taizhou Univ, Sch Pharmaceut Sci, Jiaojiang 318000, Zhejiang, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 43期
关键词：
ENANTIOSELECTIVE TOTAL-SYNTHESIS; STRUCTURE REVISION; CYCLOADDITION; DERIVATIVES;
D O I：
10.1039/d2ob01368a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile synthetic protocol for the preparation of spiro diheterocycles from easily available 2 '-aminoacetophenones, isocyanates and 1,4-benzoquinones or quinone monoimines under mild conditions has been developed. This multi-component transformation is characterized by efficient construction of two heterocycles and one valuable quaternary carbon in one pot via an in situ cyclization-respiroannulation strategy. Moreover, this reaction showed a broad substrate scope, and generated diverse five-membered oxaspiros.
引用
收藏
页码：8461 / 8464
页数：4
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  • [21] Highly Enantioselective [3+2] Annulation of Indoles with Quinones to Access Structurally Diverse Benzofuroindolines
    Liu, Qiong-Jie
    Zhu, Jun
    Song, Xiang-Yang
    Wang, Lijia
    Wang, Sunewang R.
    Tang, Yong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (14) : 3810 - 3814
  • [22] Potassium Trinitromethanide as a 1,1-Ambiphilic Synthon Equivalent: Access to 2-Nitroarenofurans
    Osyanin, Vitaly A.
    Osipov, Dmitry V.
    Demidov, Maxim R.
    Klimochkin, Yuri N.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) : 1192 - 1198
  • [23] Employing Visible-Light Photoredox Catalysis in Multicomponent- Multicatalyst Reactions: One-Pot Synthesis of Spiroquinazolin-2-(thi)ones
    Pan, Zhentao
    Yang, Xuancheng
    Chen, Bo
    Shi, Shuaijun
    Liu, Tong
    Xiao, Xuqiong
    Shen, Linlin
    Lou, Li
    Ma, Yongmin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05) : 3596 - 3604
  • [24] Eco-friendly construction of spiroquinazolin-2-(thi)ones and quinolin-(thio)ureas via Fe(iii)-catalyzed multi-component domino double [4+2] annulations
    Pan, Zhentao
    Shi, Shuaijun
    Yang, Xuancheng
    Xiao, Xuqiong
    Zhang, Wangqin
    Wang, Shiliang
    Ma, Yongmin
    [J]. GREEN CHEMISTRY, 2021, 23 (08) : 2944 - 2949
  • [25] Bioactive benzofuran derivatives: An insight on lead developments, radioligands and advances of the last decade
    Radadiya, Ashish
    Shah, Anamik
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 : 356 - 376
  • [26] Polycyclic heterocycles by condensation of 1,4-benzoquinone analogs and nucleophiles
    Singh, Rashmi
    Prakash, Rashmi
    Dehaen, Wim
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 135, 2021, 135 : 319 - 410
  • [27] DEAD-Mediated Oxidative Ugi/Aza-Wittig Reaction for the Synthesis of 5-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-1,3,4-oxadiazoles Starting from (N-Isocyanimine)triphenylphosphorane
    Sun, Mei
    Zhao, Long
    Yu, Yan-Ling
    Ding, Ming-Wu
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (07): : 1365 - 1371
  • [28] Combining Organocatalysis and Iodine Catalysis: One-Pot Sequential Catalytic Synthesis of Chiral Spirodihydrobenzofuran Pyrazolones and Spirodihydrobenzofuran Oxindoles
    Tang, Cheng-Ke
    Zhou, Zhan-Yu
    Xia, Ai-Bao
    Bai, Liang
    Liu, Jie
    Xu, Dan-Qan
    Xu, Zhen-Yuan
    [J]. ORGANIC LETTERS, 2018, 20 (18) : 5840 - 5844
  • [29] Visible-light-induced photoredox-catalyzed synthesis of benzimidazo [2,1-a]iso-quinoline-6(5H)-ones
    Wang, Bin
    Zou, Long
    Wang, Lei
    Sun, Manman
    Li, Pinhua
    [J]. CHINESE CHEMICAL LETTERS, 2021, 32 (03) : 1229 - 1232
  • [30] A Synthetic Protocol for the Construction of Chroman-Spiroquinazolin(thi)one Framework via a Metal-Free, Three-Component, Domino, Double Annulations
    Wang, Lingfeng
    Li, Song
    Xiao, Xuqiong
    Xu, Weiming
    Zhang, Pengfei
    Ma, Yongmin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (04) : 855 - 864
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