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
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
  • [31] 4-Hydroxy-3-[(4-hydroxy-6-methyl-2-oxo-3,6-dihydro-2H-pyran-3-yl)(3-thienyl)methyl]-6-methyl-3,6-dihydro-2H-pyran-2-one
    Asad, Mohammad
    Oo, Chuan-Wei
    Osman, Hasnah
    Hemamalini, Madhukar
    Fun, Hoong-Kun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O494 - U1773
  • [32] Preparation and Reactions of 2-Methyl-7-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-5-arylthiazolo[3,2-a]-pyrimido[4,5-d]oxazin-4(5H)-one
    Youssef, Mohamed Salah K.
    Abbady, Mohamed S.
    Ahmed, Ragaa A.
    Omar, Ahmed A.
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (07) : 1473 - 1482
  • [33] REGIOSELECTIVE ONE-POT SYNTHESIS OF 5-CHLORO-3-METHYL-8-TRIFLUOROMETHYL-4H-1, 4-BENZOTHIAZINES
    Ankodia, Vandana
    Sharma, Praveen Kumar
    Sharma, Kailash
    Kumar, M.
    Gupta, Archana
    HETEROCYCLIC COMMUNICATIONS, 2009, 15 (02) : 127 - 133
  • [34] Preparative synthesis of 2,2-dimethyl-5-(trifluoroacetyl)-1,3-dioxane-4,6-dione (2-trifluoroacetyl Meldrum's acid) and 2,2-dimethyl-6-(trifluoromethyl)-4H-1,3-dioxin-4-one and their synthetic usefulness as (trifluoroacetyl)ketene precursors
    Sevenard, Dmitri V.
    Didenko, Andrey V.
    Lorenz, Denis
    Vorobiev, Michael
    Stelten, Johannes
    Wicks, Thomas
    Sosnovskikh, Vyacheslav Ya.
    TETRAHEDRON, 2017, 73 (11) : 1495 - 1502
  • [35] Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H-Benzo[d][1,3]oxazin-4-ones and 4-Benzylidene-2-aryloxazol-5(4H)-ones
    Wang, Long
    Xie, Yi-Bi
    Huang, Nian-Yu
    Yan, Jia-Ying
    Hu, Wei-Min
    Liu, Ming-Guo
    Ding, Ming-Wu
    ACS CATALYSIS, 2016, 6 (06): : 4010 - 4016
  • [36] Synthesis, structure, and stereochemical non-rigidity of bis[(2,2-dimethyl-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)methyl]dichlorosilane and -germane
    Negrebetsky, Vad. V.
    Kramarova, E. P.
    Arkhipov, D. E.
    Korlyukov, A. A.
    Shipov, A. G.
    Baukov, Yu. I.
    RUSSIAN CHEMICAL BULLETIN, 2015, 64 (08) : 1808 - 1813
  • [37] Convenient selective synthesis of 5,7,8,9-tetrahydro-4H,6H-chromeno[2,3-d][1,3]oxazin-4-ones
    Litvinov, Yu. M.
    Shestopalov, A. M.
    RUSSIAN CHEMICAL BULLETIN, 2009, 58 (02) : 479 - 481
  • [38] Base-Catalyzed Nucleophilic Addition Reaction of Indoles with Vinylene Carbonate: An Approach to Synthesize 4-Indolyl-1,3-dioxolanones
    Chen, Xia
    Zhou, Xiao-Yu
    Bao, Ming
    MOLECULES, 2023, 28 (21):
  • [39] Novel 2-phenyl-6-phenylethynyl-4-(trifluoromethyl)quinolines: Synthesis by Sonogashira cross-coupling reaction and their evaluation as liquid crystals
    Rodrigues, Melissa B.
    Halfen, Renato A. P.
    Feitosa, Sarah C.
    Frizzo, Clarissa P.
    Martins, Marcos A. P.
    Zanatta, Nilo
    Merlo, Aloir A.
    Bonacorso, Helio G.
    JOURNAL OF MOLECULAR LIQUIDS, 2019, 287
  • [40] SYNTHESIS OF 1,3,4-OXADIAZOL-2-YL-METHYL-4H-BENZO [1,4] OXAZIN-3-ONES
    Rajitha, Ch.
    Vineel, B. G.
    Venkataiah, S.
    Dubey, P. K.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 24 (03) : 321 - 324