Facile Domino Access to Unexpected Alkyl 3-Substituted-2-hydroxy-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates

被引：1

作者：

Zhang, Ya-Ru ^{[1
]}

Huang, Xiao ^{[1
]}

Xu, Dong-Cheng ^{[1
]}

Xie, Jian-Wu ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Dept Chem & Life Sci, Jinhua 321004, Peoples R China

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2013年 / 66卷 / 08期

基金：

中国国家自然科学基金;

关键词：

1,3-DICARBONYL COMPOUNDS; ALPHA-HYDROXYLATION; 4-ALKYL-2-HYDROXY-3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXAZINE-2-CARBOXYLATES; CONSTRUCTION; OXYGENATION; DERIVATIVES; OXIDATION; C-1027;

D O I：

10.1071/CH13103

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new domino alkylation-cyclization-air-oxidation of 2-halo-1,3-dicarbonyl compounds with 2-aminophenols promoted by caesium salts under aerobic conditions has been developed. Unexpected alkyl 3-substituted-2-hydroxy-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates, rather than normal ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate, were exclusively obtained under mild conditions. A plausible mechanism for this unprecedented reaction is also given.

引用

页码：959 / 962

页数：4

共 50 条

[31] Asymmetric synthesis of 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides catalyzed by scandium(III)-inda-Pybox
Du, Peng
Zhou, Haifeng
Sui, Yuebo
Liu, Qixing
Zou, Kun
TETRAHEDRON, 2016, 72 (12) : 1573 - 1578
[32] Diastereoselective acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines with 2-phenoxy carbonyl chlorides
Vakarov, Sergey A.
Gruzdev, Dmitry A.
Sadretdinova, Liliya Sh.
Chulakov, Evgeny N.
Pervova, Marina G.
Ezhikova, Marina A.
Kodess, Mikhail I.
Levit, Galina L.
Krasnov, Victor P.
TETRAHEDRON-ASYMMETRY, 2015, 26 (5-6) : 312 - 319
[33] AgNO3 Catalyzed Regio-Selective Synthesis of 3-Alkyl/Aryl-idene-3,4-dihydro-4-tosyl-2H-1,4-Benzoxazine: Novel Anti-Tubercular Scaffolds
Karunanidhi, Sivanandhan
Karpoormath, Rajshekhar
Bera, Milan
Rane, Rajesh A.
Palkar, Mahesh B.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (05) : 1611 - 1616
[34] Reaction of 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with substituted acetamides of 3,4-dihydroisoquinolines
Konovalova, V. V.
Kharitonova, A. V.
Shklyaev, Yu V.
Maslivets, A. N.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (11) : 1566 - 1571
[35] Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate
Ismail, El Fekki
Ali, Ibrahim A. I.
Fathalla, Walid
Alsheikh, Amer A.
El Tamney, El Said
ARKIVOC, 2017, : 104 - 120
[36] Domino reaction of (2-haloethyl)polyfluorophenyl sulfides, sulfoxides, and sulfones with ammonia or amines: one-pot synthesis of 3,4-dihydro-2H-1,4-benzothiazines polyfluorinated at the benzene ring and the corresponding 1-oxides and 1,1-dioxides
Kondratyev, Andrey S.
Shteingarts, Vitalij D.
Litvak, Vladimir V.
Tretyakov, Evgeny V.
Tkachev, Alexey V.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (12) : 1350 - 1361
[37] A Straightforward Approach to Substituted 2-(Hydroxymethyl)-2,3-dihydrofuro[2,3-b] pyridines and 3-Hydroxy-3,4-dihydro-2H-pyrano[ 2,3-b] pyridines
Hajbi, Youssef
Suzenet, Franck
Khouili, Mostafa
Lazar, Said
Guillaumet, Gerald
SYNTHESIS-STUTTGART, 2010, (08): : 1349 - 1355
[38] N-alkyl imidazole-based homonuclear coordination complex as a neutral organocatalyst for the faster and efficient construction of 3,4-dihydro-2H-1,3-oxazine scaffold
Yildirim, Ayhan
Goker, Mustafa
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (12)
[39] Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates
Li Fengyun
Gong Jianing
Liu Jingbo
Li Yuxin
Li Zhengming
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2020, 36 (06) : 1190 - 1195
[40] Facile Construction of 3,4-dihydro-2H-1,2,4-Benzothiadiazine 1,1-Dioxides via Redox-Neutral Cascade Condensation/[1,7]-Hydride Transfer/Cyclization
Xing, Yingying
Dong, Fengying
Yin, Xiangcong
Wang, Liang
Li, Shuai-Shuai
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (11) : 1787 - 1792

← 1 2 3 4 5 →