Synthesis and thermal reactions of N-(2,3-epoxypropyl)diphenylamine

被引：0

作者：

Barvainiene B. ^{[1
,2
]}

Stanisauskaite A. ^{[1
]}

Getautis V. ^{[1
]}

机构：

[1] Department of Organic Chemistry, Kaunas University of Technology

来源：

Chemistry of Heterocyclic Compounds | 2007年 / 43卷 / 06期

关键词：

3-hydroxy-1-phenyl-1,2,3,4- tetrahydroquinoline; 3-hydroxymethyl-1-phenylindoline; Cyclization; N-(2,3-epoxypropyl)diphenylamine;

D O I：

10.1007/s10593-007-0117-7

中图分类号：

学科分类号：

摘要：

The synthesis of N-(2,3-epoxypropyl)diphenylamine is reported. It was found that thermal opening of the oxirane ring of N-(2,3-epoxypropyl)diphenylamine occurred both at the secondary and the tertiary carbon atoms but the basic reaction product is 3-hydroxy-1-phenyl-1,2,3,4-tetrahydroquinoline. © 2007 Springer Science+Business Media, Inc.

引用

页码：718 / 721

页数：3

共 50 条

[41] A practical mild, one-pot, regiospecific synthesis of 2,3-disubstituted indoles via consecutive Sonogashira and Cacchi reactions [J].

Lu, Bruce Z. ;

Zhao, Wenyi ;

Wei, Han-Xun ;

Dufour, Marine ;

Farina, Vittorio ;

Senanayake, Chris H. .

ORGANIC LETTERS, 2006, 8 (15) :3271-3274

[42] Iodine- mediated intramolecular amination of ketones: the synthesis of 2-acylindoles and 2-acylindolines by tuning N- protecting groups [J].

Gao, Wen-Chao ;

Jiang, Shan ;

Wang, Ruo-Lin ;

Zhang, Chi .

CHEMICAL COMMUNICATIONS, 2013, 49 (43) :4890-4892

[43] Multicatalytic Beckmann rearrangement of 2-hydroxylarylketone oxime: Switchable synthesis of benzo[d]oxazoles and N-(2-hydroxylaryl)amides [J].

Li, Zhen ;

Fang, Chengtao ;

Zheng, Yannan ;

Qiu, Guanyinsheng ;

Li, Xiaofang ;

Zhou, Hongwei .

TETRAHEDRON LETTERS, 2018, 59 (44) :3934-3937

[44] Indole as Neutral Leaving Group in Silver Nitrate Induced Cyclization Reactions of N-{2-[Alkynyl(hetero)aryl]methylene}indolin-1-amines for the Synthesis of Annulated Pyridine Derivatives [J].

Ghavtadze, Nugzar ;

Froehlich, Roland ;

Wuerthwein, Ernst-Ulrich .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (09) :1787-1797

[45] Asymmetric Synthesis of δ-Chloro-β-amino-N-sulfinyl Imidates as Versatile Chiral Building Blocks for the Synthesis of 2,3-Disubstituted Piperidines [J].

Semina, Elena ;

Colpaert, Filip ;

Van Hecke, Kristof ;

De Kimpe, Norbert ;

Mangelinckx, Sven .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (22) :4847-4859

[46] Radical Additions of Arenethiols to Ynamides for the Selective Synthesis of N-[(Z)-2-(Arylsulfanyl)-1-alkenyl]amides [J].

Sato, Akinori ;

Yorimitsu, Hideki ;

Oshima, Koichiro .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (03) :570-576

[47] Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation [J].

Ji, Cong-Bin ;

Xie, Ding-Xiong ;

Chen, Mei ;

Lan, Ye-Ying ;

Zhang, Bao-Hua ;

Yang, Ji-Ying ;

Kang, Zheng-Hui ;

Chen, Shu-Jie ;

Zhang, Yu-Wei ;

Liu, Yun-Lin .

CHINESE CHEMICAL LETTERS, 2025, 36 (07)

[48] New Reactions of N-tert-Butylimines; Formation of N-Heterocycles by Methyl Radical Elimination on Flash Vacuum Thermolysis of N-Benzylidene- and N-(2-Pyridylmethylidene)-tert-butylamines [J].

Vu, Thien Y. ;

Chrostowska, Anna ;

Thi Kieu Xuan Huynh ;

Khayar, Said ;

Dargelos, Alain ;

Justyna, Katarzyna ;

Pasternak, Beata ;

Lesniak, Stanislaw ;

Wentrup, Curt .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (44) :14983-14988

[49] Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles [J].

Ouizem, Sabrina ;

Chemla, Fabrice ;

Ferreira, Franck ;

Perez-Luna, Alejandro .

SYNLETT, 2012, (09) :1374-1378

[50] I- catalyzed cascade annulation of 2-(pyridin-2-yl)acetate derivatives with N , N- dimethylenamine 2 ketones: Site-selective synthesis of functionalized indolizines [J].

Li, Yuan -Da ;

Zhang, Wei-Min ;

Zhao, Ke-Hua ;

Zhang, Cong-Hai ;

Yan, Sheng-Jiao .

TETRAHEDRON, 2024, 159

← 1 2 3 4 5 →