Reaction of 4-methyl-2-trifluoromethyl-1,3-oxazin-6-one with indoles

被引：2

作者：

Usachev, Sergey A. ^{[1
]}

Tabatchikova, Kristina M. ^{[1
]}

Sevenard, Dmitri V. ^{[2
]}

Sosnovskikh, Vyacheslav Ya. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci & Math, 51 Lenin Ave, Ekaterinburg 620000, Russia

[2] Hansa Fine Chem GmbH, Bremen Innovat & Technol Ctr, 1 Fahrenheitstr, D-28359 Bremen, Germany

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2018年 / 54卷 / 09期

基金：

俄罗斯基础研究基金会;

关键词：

indoles; 2-(indol-3-yl)-4-methyl-2-trifluoromethyl-2; 3-dihydro-1; 3-oxazin-6-ones; 1; 3-oxazin-6-one; pyrroles; nucleophilic addition; 1,3-OXAZIN-6-ONES; 4-ARYL-6-TRIFLUOROMETHYL-2-PYRONES; DERIVATIVES;

D O I：

10.1007/s10593-018-2359-y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of indoles to 4-methyl-2-trifluoromethyl-1,3-oxazin-6-one in an acidic medium proceeds at the C-2 atom and leads to 2-(indol-3-yl)-4-methyl-2-trifluoromethyl-2,3-dihydro-1,3-oxazin-6-ones in 67-83% yields. Pyrroles and N,N-dimethylaniline either do not enter into a reaction of this type or form the addition products in very low yields (6-12%).

引用

页码：848 / 851

页数：4

共 50 条

[21] Synthesis of 2,3-Dihydro-1,3-oxazin-4-ones via a Mild Formal [4+2] Cycloaddition of Acylketenes with Aldimines
Moazami, Yasamin
Pierce, Joshua G.
SYNTHESIS-STUTTGART, 2015, 47 (21): : 3363 - 3370
[22] Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-(4-((2-methyl-6-(trifluoromethyl) pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
Pan, Nian-Juan
Yan, Chang
Fei, Qiang
Wu, Wen-Neng
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2023, 238 (05): : 903 - 905
[23] 6-Methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazolyl)pyrimidin-4(1H)-one as CH Acid in Michael Reaction
Erkin, A. V.
Krutikov, V. I.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2009, 79 (07) : 1525 - 1531
[24] Thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes: divergent synthesis from reaction of 2-trifluoromethyl-1,3-conjugated enynes with sulfur nucleophiles
Cheng, Huayu
Zhou, Xiaofan
Hu, Anjing
Ding, Shiteng
Wang, Yimo
Xiao, Yuanjing
Zhang, Junliang
RSC ADVANCES, 2018, 8 (59): : 34088 - 34093
[25] Recyclable Copper-Catalyzed Cascade Coupling/Condensation/ Deacylation Reaction of 2′-Halotrifluoroacetanilides with β-Keto Esters toward 2-(Trifluoromethyl)indoles
Wang, Yan
Ye, Qian
Cai, Mingzhong
SYNTHESIS-STUTTGART, 2025, 57 (04): : 754 - 763
[26] Synthesis of 6-hydroxy-5,6-dihydro-2-pyrones and -pyridones by reaction of 4-aryl-6-trifluoromethyl-2-pyrones with water, hydrazine, and hydroxylamine
Usachev, Sergey A.
Usachev, Boris I.
Sosnovskikh, Vyacheslav Ya.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (12) : 1294 - 1301
[27] 2-Cyano-6-(trifluoromethyl)-4H-pyran-4-one: A novel versatile CF3-containing building block
Usachev, Boris I.
Obydennov, Dmitrii L.
Roeschenthaler, Gerd-Volker
Sosnovskikh, Vyacheslav Ya.
JOURNAL OF FLUORINE CHEMISTRY, 2012, 137 : 22 - 26
[28] A one-pot synthesis of 4-aryl-2-methyl-1,2,3,4-tetrahydro-γ-carbolines from 5-aryloxazolidines and indoles via a Mannich/Friedel-Crafts sequence
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Y.
TETRAHEDRON LETTERS, 2014, 55 (44) : 6121 - 6124
[29] 2-Amino-6-methyl-1,3-benzothiazole-decanedioic acid (2/1)
Shi, Xiang-Jun
Wang, Zhi-Chao
Chen, Qiang
Zhao, Xiao-Jun
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2188 - U2318
[30] 2-(((4-(Trifluoromethyl)quinolin-6-yl)amino)methyl)phenols: Synthesis, optical properties, thermal, and electrochemical behavior
Rocha, Inaia O.
Ketzer, Alex
Luz, Fabio M.
Vieira, Jean C. B.
Frizzo, Clarissa P.
Martins, Marcos A. P.
Zanatta, Nilo
Bonacorso, Helio G.
Iglesias, Bernardo A.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2024, 453

← 1 2 3 4 5 →