Cesium-Carbonate-Mediated Benzalation of Substituted 2-Aryl-3-nitro-2H-chromenes with Substituted 4-Benzylidene-2-phenyloxazol-5(4H)-ones

被引:14
作者
Dai, Chenlu [1 ]
Luo, Naili [1 ]
Wang, Shan [1 ]
Wang, Cunde [1 ]
机构
[1] Yangzhou Univ, Sch Chem & Chem Engn, 180 Siwangting St, Yangzhou 225002, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES;
D O I
10.1021/acs.orglett.9b00776
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cs2CO3-mediated domino benzalation reaction with a variety of 2-aryl-3-nitro-2H-chromenes and 4-benzylidene-2-phenyloxazol-5(4H)-ones has been realized. The reaction proceeds smoothly with a broad substrate scope, thus providing a variety of substituted (Z)-4-((Z)-benzylidene)chroman-3-one oximes in moderate to high yields, which were easily transformed into biologically important 4H-chromeno[3,4-c]isoxazoles.
引用
收藏
页码:2828 / 2832
页数:5
相关论文
共 66 条
[1]   KOtBu-Mediated Aza-Michael Addition of Aromatic Amines or N-Phenylurea to 3-Nitro-2-phenyl-2H-chromenes and Sequential Aerobic Dehydrogenation [J].
Alsharif, Meshari A. ;
Khan, Danish ;
Mukhtar, Sayeed ;
Alahmdi, Mohammed Issa ;
Ahmed, Naseem .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (26) :3454-3463
[2]   3-Nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes: synthesis and reactions with nucleophiles [J].
Barkov, Alexey Yu. ;
Korotaev, Vladislav Yu. ;
Kotovich, Ivan V. ;
Zimnitskiy, Nikolai S. ;
Kutyashev, Igor B. ;
Sosnovskikh, Vyacheslav Ya. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (10) :814-822
[3]   Organocatalytic and enantioselective Michael reaction of malonates to 3-Nitro-2H-chromenes [J].
Chen, Wei-Yi ;
Li, Ping ;
Xie, Jian-wu ;
Li, Xin-Sheng .
CATALYSIS COMMUNICATIONS, 2011, 12 (06) :502-504
[4]  
Cling X, 2018, SYNTHESIS-STUTTGART, V50, P1350
[5]  
Ellis G.P., 1977, CHEM HETEROCYCL COM+, V31, P455
[6]   Diversified Synthesis of Furans by Coupling between Enols/1,3-Dicarbonyl Compounds and Nitroolefins: Direct Access to Dioxa[5]helicenes [J].
Ghosh, Monoranjan ;
Santra, Sougata ;
Mondal, Pallab ;
Kundu, Dhiman ;
Hajra, Alakananda .
CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (11) :2525-2536
[7]   Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction [J].
Guo, Zhi-Wei ;
Li, Xin-Sheng ;
Zhu, Wei-Dong ;
Xie, Jian-Wu .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (35) :6924-6932
[8]   Antioxidant and antiviral activities of plastoquinones from the brown alga Sargassum micracanthum, and a new chromene derivative converted from the plastoquinones [J].
Iwashima, M ;
Mori, J ;
Ting, X ;
Matsunaga, T ;
Hayashi, K ;
Shinoda, D ;
Saito, H ;
Sankawa, U ;
Hayashi, T .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2005, 28 (02) :374-377
[9]   Asymmetric Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes [J].
Jia, Yang ;
Yang, Wen ;
Du, Da-Ming .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (24) :4739-4746
[10]   Synthesis of 3-Substituted Chromones and Quinolones from Enaminones [J].
Joussot, Jessie ;
Schoenfelder, Angele ;
Larquetoux, Laurent ;
Nicolas, Marc ;
Suffert, Jean ;
Blond, Gaelle .
SYNTHESIS-STUTTGART, 2016, 48 (19) :3364-3372