Metal-free [3+3] benzannulation of 1-indanylidene-malononitrile with Morita-Baylis-Hillman carbonates: direct access to functionalized fluorene and fluorenone derivatives

被引：20
|
作者：
Xie, Ya-Sa [1 ]
Huang, Run-Feng [2 ]
Li, Ran [1 ]
Zhang, Chuan-Bao [1 ]
Fu, Ji-Ya [1 ,3 ]
Zhao, Li-Li [2 ]
Yuan, Jin-Fang [1 ]
机构：
[1] Henan Univ, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China
[2] Nanjing Tech Univ, Inst Adv Synth, Sch Chem & Mol Engn, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Nanjing 211816, Jiangsu, Peoples R China
[3] Henan Univ, Inst Fine Chem & Engn, Kaifeng 475004, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 13期
基金：
中国国家自然科学基金;
关键词：
CONSTRUCTION; ANNULATIONS; DIVERSE; ALKYLATION; IMINES;
D O I：
10.1039/d0cc00143k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient [3+3] benzannulation of Morita-Baylis-Hillman carbonates with 1-indanylidenemalononitrile was achieved under metal-free reaction conditions selectively delivering a wide range of functional multi-substituted fluorene or fluorenone compounds in high yields, respectively (up to 86% yield). Moreover, experiments and quantum chemical calculations were also performed to study the mechanism of the transformation.
引用
收藏
页码：1948 / 1951
页数：4
相关论文
共 50 条
  • [41] Synthesis of functionalized spiro[indanone-benzazepine] scaffolds via [4+3] annulation reaction of N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita-Baylis-Hillman carbonates
    Wang, Kai-Kai
    Ye, Jun-Wei
    Jia, Jun
    Li, Ya-Fei
    Yao, Wei-Wei
    Li, Lan-Xin
    Zhao, Su-Miao
    Xu, Yan
    Chen, Rongxiang
    TETRAHEDRON, 2024, 150
  • [42] A short time isomerisation for the synthesis of 3-ylideneoxindoles from Morita-Baylis-Hillman adduct of isatin derivatives with 1-hexyn-3-ol using FeCl3 and K-10 clay
    Vaithiyanathan, Vadivel
    Ravichandran, Ganesan
    TETRAHEDRON LETTERS, 2021, 75
  • [43] Regio- and diastereoselective construction of 1′,2′-(dihydrospiro[indoline-3,3′-pyrrol]-2′-yl)acrylates through phosphine-catalyzed [4+1] annulation of Morita-Baylis-Hillman carbonates with oxindole-derived α, β-unsaturated imines
    Lei, Yu
    Zhang, Xiao-Nan
    Yang, Xue-Yan
    Xu, Qin
    Shi, Min
    RSC ADVANCES, 2015, 5 (61) : 49657 - 49661
  • [44] Metal-Free Coupling of Azoles with 2-and 3-Haloindoles Providing Access to Novel 2-or 3-(Azol-1-yl)indole Derivatives
    Poirier, Martin
    Goudreau, Sebastien
    Poulin, Jason
    Savoie, Jolaine
    Beaulieu, Pierre L.
    ORGANIC LETTERS, 2010, 12 (10) : 2334 - 2337
  • [45] Highly regioselective and metal-free γ-addition of β-keto esters to isatins, catalyzed by DABCO: direct access to novel class of diversely functionalized 3-hydroxy-2-oxindole scaffolds
    Thakur, Pramod Bhagwan
    Sirisha, Katukuri
    Sarma, Akella Venkata Subrahmanya
    Nanubolu, Jagadeesh Babu
    Meshram, Harshadas Mitaram
    TETRAHEDRON, 2013, 69 (31) : 6415 - 6423
  • [46] Metal-free direct C(sp~3)-H functionalization of 2-alkylthiobenzoic acid to access 1,3-benzooxathiin-4-one
    Ke Yang
    Yi Li
    Mengjie Song
    Shengfei Dai
    Zheng-Yi Li
    Xiaoqiang Sun
    ChineseChemicalLetters, 2021, 32 (01) : 146 - 149
  • [47] Metal-free direct C(sp3)-H functionalization of 2-alkylthiobenzoic acid to access 1,3-benzooxathiin-4-one
    Yang, Ke
    Li, Yi
    Song, Mengjie
    Dai, Shengfei
    Li, Zheng-Yi
    Sun, Xiaoqiang
    CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 146 - 149
  • [48] Metal-free sequential dual oxidative amination of C(sp3)-H bonds: A direct approach to benzothiadiazine 1,1-dioxide derivatives
    Wang, Dongyin
    Li, Xiaokang
    Zhao, Yongli
    Chen, Junmin
    SYNTHETIC COMMUNICATIONS, 2017, 47 (04) : 351 - 356
  • [49] Transition Metal-Free α-C(sp3)-H Bond Functionalization of Amines by Oxidative Cross Dehydrogenative Coupling Reaction: Simple and Direct Access to C-4-Alkylated 3,4-Dihydroquinazoline Derivatives
    Kumar, R. Arun
    Saidulu, G.
    Prasad, K. Rajendra
    Kumar, G. Sathish
    Sridhar, B.
    Reddy, K. Rajender
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2985 - 2991
  • [50] Metal-free, Tf2NH-catalyzed 1, 6-conjugate addition of imidazopyridine to para-quinone methides: Easy access to C3-functionalized triarylmethane imidazopyridine
    Khonde, Nilesh S.
    Said, Madhukar S.
    Sabane, Jagjivan K.
    Gajbhiye, Jayant M.
    Kumar, Pradeep
    TETRAHEDRON, 2021, 101
12345