A Lewis acid-catalyzed tandem reaction enabling 2-arylglycerol derivative as a versatile 1,3-biselectrophile for the synthesis of 4H-chromenes and 2-pyridinones

被引：0

作者：

Shaomin Chen ^{[1
]}

Tianjian Zhang ^{[1
]}

Zhenhua Xu ^{[1
]}

Bo You ^{[1
]}

Minghao Li ^{[1
]}

Yanlong Gu ^{[1
,2
,3
]}

机构：

[1] Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure,School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology

[2] School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University

[3] State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics

来源：

Chinese Chemical Letters | 2023年 / 34卷 / 09期

基金：

中国国家自然科学基金;

关键词：

D O I：

暂无

中图分类号：

O621.251 [];

学科分类号：

摘要：

Acid-catalyzed tandem reactions were established by employing a novel class of 2-arylglycerol derivative,5-aryl-1,3-dioxan-5-ol, as versatile 1,3-biselectrophile. In the reactions, 5-aryl-1,3-dioxan-5-ol works like atropaldehydes or 2-aryl malondialdehydes, and can react with 2-naphthols and β-keto amides, allowing the synthesis of 4H-chromenes and 5-aryl-2-pyridinones. High yields, good functional group tolerance,broad substrate scope and simple reaction operation make this protocol attractive.

引用

页码：165 / 168

页数：4

共 50 条

[1] A Lewis acid-catalyzed tandem reaction enabling 2-arylglycerol derivative as a versatile 1,3-biselectrophile for the synthesis of 4 H -chromenes and 2-pyridinones
Chen, Shaomin
Zhang, Tianjian
Xu, Zhenhua
You, Bo
Li, Minghao
Gu, Yanlong
CHINESE CHEMICAL LETTERS, 2023, 34 (09)
[2] Unexpected tandem ylide annulation reaction for controllable synthesis of 2H-chromenes and 4H-chromenes
Ye, Long-Wu
Sun, Xiu-Li
Zhu, Chun-Yin
Tang, Yong
ORGANIC LETTERS, 2006, 8 (17) : 3853 - 3856
[3] Copper-catalyzed tandem reaction of 2-bromobenzyl bromides with 1,3-dicarbonyl compounds leading to 4H-chromenes
Zhang, Xin Ying
Fang, Liang Liang
Liu, Nan
Wu, Hua Yue
Fan, Xue Sen
CHINESE CHEMICAL LETTERS, 2012, 23 (10) : 1129 - 1132
[4] Copper-catalyzed tandem reaction of 2-bromobenzyl bromides with 1,3-dicarbonyl compounds leading to 4H-chromenes
Xin Ying Zhang~(a
Chinese Chemical Letters, 2012, 23 (10) : 1129 - 1132
[5] 4H-Chromenes as 1,3-bielectrophiles in the reaction with 2-aminobenzimidazole: synthesis of pyrimido [1,2-a] benzimidazoles
Osyanin, Vitaly A.
Osipov, Dmitry, V
Korzhenko, Kirill S.
Demidov, Oleg P.
Klimochkin, Yuri N.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (05) : 588 - 593
[6] 4H-Chromenes as 1,3-bielectrophiles in the reaction with 2-aminobenzimidazole: synthesis of pyrimido[1,2-a]benzimidazoles
Vitaly А. Osyanin
Dmitry V. Osipov
Kirill S. Korzhenko
Oleg P. Demidov
Yuri N. Klimochkin
Chemistry of Heterocyclic Compounds, 2021, 57 : 588 - 593
[7] APPLICATION OF THE LEWIS ACID-CATALYZED [4+2]CYCLOADDITION REACTION TO SYNTHESIS OF NATURAL QUINOLINE ALKALOIDS
KAMETANI, T
TAKEDA, H
SUZUKI, Y
KASAI, H
HONDA, T
HETEROCYCLES, 1986, 24 (12) : 3385 - 3395
[8] Lewis acid-controlled divergent condensation of 1,1-bis(methylthio)-2 nitroethylene and salicylaldehydes for the synthesis of 3-nitrocoumarins and 4H-chromenes
Han, Li
Quan, Xiaocao
Shao, Xusheng
Xu, Xiaoyong
Li, Zhong
TETRAHEDRON LETTERS, 2023, 118
[9] A FACILE LEWIS ACID-CATALYZED DIELS-ALDER REACTION OF 2-TRIMETHYLSILYL-SUBSTITUTED 1,3-BUTADIENES
NIKAM, SS
WANG, KK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1984, 188 (AUG): : 61 - ORGN
[10] Lewis acid-catalyzed Wolff cyclocondensation in the synthesis of (1H-1,2,3-triazolyl) furoxans
Fershtat, Leonid L.
Radzhabov, Maxim R.
Romanova, Anna A.
Ananyev, Ivan V.
Makhova, Nina N.
ARKIVOC, 2017, : 140 - 150

← 1 2 3 4 5 →