Formal [4+2] annulation of enaminones and cyanomethyl sulfur ylide: one-pot access to polysubstituted pyridin-2(1H)-ones

被引：26

作者：

Zhang, Qian ^{[1
]}

Liu, Xu ^{[1
]}

Xin, Xiaoqing ^{[1
]}

Zhang, Rui ^{[1
]}

Liang, Yongjiu ^{[1
]}

Dong, Dewen ^{[1
]}

机构：

[1] Chinese Acad Sci, Changchun Inst Appl Chem, Changchun 130022, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 97期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; (20S)-CAMPTOTHECIN FAMILY; EFFICIENT SYNTHESIS; CLOSING METATHESIS; SYNTHETIC METHODS; CONCISE SYNTHESIS; BRASSARDS DIENE; DELTA-LACTAMS; ACID;

D O I：

10.1039/c4cc06665k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and efficient one-pot synthesis of polysubstituted pyridin-2(1H)-ones from readily available enaminones and the cyanomethyl sulfonium bromide salt in the presence of cesium carbonate is developed, and a mechanism involving sequential nucleophilic vinylic substitution (SNV), intramolecular nucleophilic cyclization and dealkylation reactions is proposed.

引用

页码：15378 / 15380

页数：3

共 50 条

[41] One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in the Presence of a Molecular Sieve Supported Lanthanum Catalyst
Magyar, Agnes
Hell, Zoltan
CATALYSIS LETTERS, 2016, 146 (06) : 1153 - 1162
[42] Three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in 2,2,2-trifluoroethanol
Khaksar, Samad
Talesh, Saeed Mohammadzadeh
COMPTES RENDUS CHIMIE, 2012, 15 (09) : 779 - 783
[43] Vilsmeier-Type Reaction of Dimethylaminoalkenoyl Cyclopropanes: One-Pot Access to 2,3-Dihydrofuro [3,2-c]pyridin-4(5H)-ones
Huang, Peng
Zhang, Ning
Zhang, Rui
Dong, Dewen
ORGANIC LETTERS, 2012, 14 (01) : 370 - 373
[44] Boron trioxide-alumina as a heterogeneous catalyst in a facile solvent free one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
Zhou, Xufeng
Cheng, Tianxing
Zheng, Xiangyong
Ke, Qiang
Wang, Xuebao
JOURNAL OF CHEMICAL RESEARCH, 2012, (04) : 213 - 215
[45] One-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones by Fe3O4@SiO2-imid-PMAn nano-catalyst under ultrasonic irradiation and reflux conditions
Esmaeilpour, Mohsen
Javidi, Jaber
Zahmatkesh, Saeed
Fahimi, Nafiseh
MONATSHEFTE FUR CHEMIE, 2017, 148 (05): : 947 - 956
[46] Phosphine(III)-Triggered One-Pot Domino Sequences towards 5,6-Dihydropyridine-2-(1H)-One and Pyridine-2(1H)-One Scaffolds
Makra, Zsofia
Madacsi, Ramona
Martinek, Tamas A.
Benyei, Attila
Puskas, Laszlo G.
Gyuris, Mario
Kanizsai, Ivan
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (06) : 1134 - 1143
[47] One-pot Syntheses of Some New 2,4(1H,3H)-quinazolinedione Derivatives in the Absence of Catalyst
Mohammadi, Ali Asghar
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (03) : 2075 - 2078
[48] One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (Thiones) Promoted by Nano-BF3•SiO2
Mirjalili, B. F.
Bamoniri, A.
Akbari, A.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2011, 8 : S135 - S140
[49] Imidazolium-Based Phosphinite Ionic Liquid as Reusable Catalyst and Solvent for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-(thio)ones
Valizadeh, Hassan
Shockravi, Abbas
HETEROATOM CHEMISTRY, 2009, 20 (05) : 284 - 288
[50] Sustainable parts-per-million level catalysis with FeIII: One-pot cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water
Dutta, Apurba
Trivedi, Priyanka
Kulshrestha, Akshay
Kumar, Arvind
Chaturvedi, Vinita
Sarma, Diganta
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (03)

← 1 2 3 4 5 →