Synthesis and reactivity of methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates

被引:3
|
作者
Sheverdov, V. P. [1 ]
Andreev, A. Yu. [1 ]
Ershov, O. V. [1 ]
Nasakin, O. E. [1 ]
Tafeenko, V. A. [2 ]
Gein, V. L. [3 ]
机构
[1] Chuvashia State Univ, Cheboksary 428015, Russia
[2] Moscow MV Lomonosov State Univ, Moscow 119991, Russia
[3] Perm State Pharmaceut Acad, Perm 614990, Russia
关键词
cyclopentenones; 5-oxopentanoic acid; 4H-pyrans; pyridines; ring opening; SPIRO-HETEROCYCLES; DERIVATIVES; FLUORINE; AGENTS;
D O I
10.1007/s10593-012-1091-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By treating arylidenemalononitriles with methyl 2,4-dioxobutanoates, derivatives of 4H-pyrans - methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates - are obtained, which are novel, promising structural components for the synthesis of carbo- and heterocycles. The reactions of these pyrans with sulfuric and hydrochloric acids, acetic anhydride, and alcohols have been studied. Novel methods have been developed for the preparation of substituted derivatives of cyclopentenone, pyrano[2,3-d]-pyrimidine, 5-oxo-3-phenylpentanoic acid, and nicotinic acid nitrile.
引用
收藏
页码:997 / 1005
页数:9
相关论文
共 50 条
  • [21] Triphenylphosphine Catalysed Facile Multicomponent Synthesis of 2-Amino-3-Cyano-6-Methyl-4-Aryl-4H-Pyrans
    Ramadoss, Harikrishnan
    Kiyani, Hamzeh
    Mansoor, Syed Sheik
    IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2017, 36 (01): : 19 - 26
  • [22] Synthesis and spectral studies of some 4H-pyran derivatives: Crystal and molecular structure of isobutyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate
    Kumar, C. Udhaya
    Sethukumar, A.
    Prakasam, B. Arul
    JOURNAL OF MOLECULAR STRUCTURE, 2013, 1036 : 257 - 266
  • [24] Synthesis of masked 2-amino-6-methyl-4-oxo-4H-pyran-3-carbaldehydes
    Denisenko, Alexander V.
    Tverdokhlebov, Anton V.
    FRENCH-UKRAINIAN JOURNAL OF CHEMISTRY, 2018, 6 (01): : 67 - 73
  • [25] Microwave-assisted liquid-phase synthesis of methyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate using functional ionic liquid as soluble support
    Yi, FP
    Peng, YQ
    Song, GH
    TETRAHEDRON LETTERS, 2005, 46 (22) : 3931 - 3933
  • [26] 3-cyano-6-(4-methoxyphenyl)-5-methyl-4-methylthio-2H-pyran-2-one
    Azim, A
    Parmar, VS
    Errington, W
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 : 1436 - 1438
  • [27] 3-Cyano-6-(4-methoxyphenyl)-5-methyl-4-methylthio-2H-pyran-2-one
    Azim, Abul
    Parmar, Virinder S.
    Errington, William
    Acta Crystallographica, Section C: Crystal Structure Communications, 1997, 53 (pt 10): : 1436 - 1438
  • [28] Synthesis and Photoreaction of 2-Amino-3-cyano-4-aryl-4H-pyrans
    Sun, Wuji
    Jiang, Yangye
    Yan, Hong
    Song, Xiuqing
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2015, 68 (02) : 273 - 281
  • [29] SYNTHESIS AND REACTIONS OF 6-ARYL AND 6-STYRYL-3-CYANO-4-METHYLTHIO-2H-PYRAN-2-ONES
    TOMINAGA, Y
    USHIROGOCHI, A
    MATSUDA, Y
    KOBAYASHI, G
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1984, 32 (09) : 3384 - 3395
  • [30] X-ray Crystallography of Methyl (6-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-4H-pyran)-3-carboxylate
    Sharma, Suresh
    Banerjee, Bubun
    Brahmachari, Goutam
    Kant, Rajni
    Gupta, Vivek K.
    CRYSTALLOGRAPHY REPORTS, 2016, 61 (07) : 1051 - 1054