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

页码：1948 / 1951

页数：4

共 16 条

[1] Phosphine-Catalyzed Domino [3+3] Cyclization of para-Quinamines with Morita-Baylis-Hillman Carbonates: Access to Hydroquinoline Derivatives
Jin, Hongxing
Lai, Jingxiong
Huang, You
ORGANIC LETTERS, 2019, 21 (08) : 2843 - 2846
[2] Lewis-Base-Catalyzed Asymmetric [3+3] Annulation Reaction of Morita-Baylis-Hillman Carbonates: Enantioselective Synthesis of Spirocyclohexenes
Yang, Wenjun
Sun, Wei
Zhang, Cheng
Wang, Qijun
Guo, Zhenyan
Mao, Biming
Liao, Jianning
Guo, Hongchao
ACS CATALYSIS, 2017, 7 (05): : 3142 - 3146
[3] 4-Dimethylaminopyridine-catalyzed [3+3] spiroannulation reactions of isatin-derived Morita-Baylis-Hillman carbonates with indoline-2-thiones
Geng, Congcong
Wei, Xingfu
Xu, Yongqiang
Liu, Jianhui
Peng, Lizeng
Wang, Baomin
TETRAHEDRON LETTERS, 2022, 102
[4] Facile synthesis of biarylmethanes and tetrasubstituted arenes via a base-mediated [3+3] benzannulation reaction of Morita-Baylis-Hillman adducts and unsaturated sulfones
Yadav, Deepak
Sharma, Sunil K.
Menon, Rajeev S.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (16) : 4073 - 4076
[5] α-Regioselective Asymmetric [3+2] Annulations of Morita-Baylis-Hillman Carbonates with Cyclic 1-Azadienes and Mechanism Elucidation
Wang, Kai-Kai
Jin, Tian
Huang, Xin
Ouyang, Qin
Du, Wei
Chen, Ying-Chun
ORGANIC LETTERS, 2016, 18 (04) : 872 - 875
[6] Substrate-controlled [4+1] and [3+2] annulations of ninhydrin-derived Morita-Baylis-Hillman carbonates to access polysubstituted furans and cyclopentenes
Wang, Kai-Kai
Li, Yan-Li
Li, Ya-Fei
Yao, Wei-Wei
Li, Lan-Xin
He, Xiao-Long
Chen, Rongxiang
CHEMICAL COMMUNICATIONS, 2024, 60 (27) : 3717 - 3720
[7] Phosphine-catalyzed asymmetric [4+1] annulation of Morita-Baylis-Hillman carbonates with dicyano-2-methylenebut-3-enoates
Zhang, Xiao-nan
Deng, Hong-Ping
Huang, Long
Wei, Yin
Shi, Min
CHEMICAL COMMUNICATIONS, 2012, 48 (69) : 8664 - 8666
[8] Asymmetric [3+2] spiroannulation of pyrazolone-derived Morita-Baylis-Hillman carbonates with alkynyl ketones: facile access to spiro[cyclopentadiene-pyrazolone] scaffolds
Wei, Xingfu
Huang, Yue
Wang, Wenyao
Wei, Shiqiang
Qu, Jingping
Wang, Baomin
CHEMICAL COMMUNICATIONS, 2022, 58 (68) : 9504 - 9507
[9] Synthesis of Chromone-Spiroindolinone-Cyclopentene Derivatives through Phosphine-Catalyzed (3+2) Annulation of Morita-Baylis-Hillman Carbonates with Oxindole-Chromones
Wang, Bo
Hu, Yimin
Guo, Hongchao
Tao, Lei
CHEMISTRYSELECT, 2022, 7 (44):
[10] Asymmetric (4+3) and (4+1) Annulations of Isatin-derived Morita-Baylis-Hillman Carbonates to Construct Diverse Chiral Heterocyclic Frameworks
Yan, Ru-Jie
Liu, Bao-Xin
Xiao, Ben-Xian
Du, Wei
Chen, Ying-Chun
ORGANIC LETTERS, 2020, 22 (11) : 4240 - 4244

← 1 2 →