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
收藏
页码：848 / 851
页数：4
相关论文
共 50 条
  • [1] Reaction of 4-methyl-2-trifluoromethyl-1,3-oxazin-6-one with indoles
    Sergey А. Usachev
    Kristina M. Tabatchikova
    Dmitri V. Sevenard
    Vyacheslav Ya. Sosnovskikh
    Chemistry of Heterocyclic Compounds, 2018, 54 : 848 - 851
  • [2] Reaction of 2-Alkoxy-4,5-diphenyl-1,3-oxazin-6-one with different alcohols and elucidation of the products
    Assadieskandar, Amir
    Amini, Mohsen
    Haukka, Matti
    Shafiee, Abbas
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (02) : 358 - 362
  • [3] Reactivity of 2-Methyl-4H-3,1-benzoxazin-4-ones and 2-Methyl-4H-pyrido [2,3-d][1,3] oxazin-4-one under Microwave Irradiation Conditions
    Prousis, Kyriakos C.
    Tzani, Andromachi
    Avlonitis, Nicolaos
    Calogeropoulou, Theodora
    Detsi, Anastasia
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (06) : 1313 - 1321
  • [4] Synthesis of 4-aryl-6-methyl-7a-(trifluoromethyl)-2,4a,5,6,7,7a-hexahydropyrano[2,3-c]pyrrol-2-ones from 4-aryl-6-(trifluoromethyl)-2-pyrones, sarcosine, and formaldehyde
    Usachev, Sergey A.
    Popova, Natal'ya V.
    Moshkin, Vladimir S.
    Sosnovskikh, Vyacheslav Ya.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (10) : 913 - 917
  • [5] Synthesis of 2H-1,4-Oxazin-3(4H)-One Utilizing Umpolung Reaction to α-Hydrazonoketone
    Mizota, Isao
    Oshima, Keiji
    Hoshiai, Nozomi
    Yamamoto, Ayaki
    Mitani, Masaki
    Batool, Rabbia
    Liu, Bo-Tau
    Shimizu, Makoto
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (03)
  • [6] Synthesis of 2-aryl-7-methyl-4-selenoxo-4H-pyrano[3,4-e][1,3]oxazin-5-one via a three-component condensation
    Rashidi, Amir
    Mosslemin, Mohammad H.
    Hassanabadi, Alireza
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2020, 196 (05) : 497 - 500
  • [7] 1,3-Dipolar cycloaddition reaction of 3-trifluoromethyl-4-diazopyrazolinones with acetylenedicarboxylates
    Zhang, Zhenhua
    Wang, Xiaowei
    Tao, Song
    Zhu, Shizheng
    TETRAHEDRON, 2012, 68 (30) : 5969 - 5978
  • [8] Synthesis and Antimicrobial Activity of 4-Hydroxy-2-[5-Nitrofuran(Thien)-2-Yl]-6h-1,3-Oxazin-6-Ones
    Chernov, N. M.
    Koshevenko, A. S.
    Yakovlev, I. P.
    Anan'eva, E. P.
    Ksenofontova, G. V.
    Shchegolev, A. E.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2017, 51 (08) : 644 - 647
  • [9] Regioselective Carbon-Carbon Bond Formation in the Reaction of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes with Indoles Promoted by Lewis Acid
    Pang, Wan
    Han, Jian Wei
    Zhao, Jing Wei
    Zhu, Shi Zheng
    SYNTHESIS-STUTTGART, 2011, (20): : 3364 - 3370
  • [10] Enantioselective Synthesis of 2-Substituted Indoles Bearing Trifluoromethyl Moiety by the Friedel-Crafts Alkylation Reaction of 4,7-Dihydroindole withN-H Trifluoromethyl Ketimines
    Uchikura, Tatsuhiro
    Suzuki, Riku
    Suda, Yusuke
    Akiyama, Takahiko
    CHEMCATCHEM, 2020, 12 (19) : 4784 - 4787
12345