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
  • [1] Synthesis and reactivity of methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates
    V. P. Sheverdov
    A. Yu. Andreev
    O. V. Ershov
    O. E. Nasakin
    V. A. Tafeenko
    V. L. Gein
    [J]. Chemistry of Heterocyclic Compounds, 2012, 48 : 997 - 1005
  • [2] Synthesis and Antiproliferative and Antimicrobial Activity of Methyl-6-Amino-3-Acyl-4-Aryl-5-Cyano-4H-Pyran-2-Carboxylates and their Derivatives
    Sheverdov, V. P.
    Andreev, A. Yu.
    Nasakin, O. E.
    Gein, V. L.
    [J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (06) : 379 - 382
  • [3] Synthesis and Antiproliferative and Antimicrobial Activity of Methyl-6-Amino-3-Acyl-4-Aryl-5-Cyano-4H-Pyran-2-Carboxylates and their Derivatives
    V. P. Sheverdov
    A. Yu. Andreev
    O. E. Nasakin
    V. L. Gein
    [J]. Pharmaceutical Chemistry Journal, 2014, 48 : 379 - 382
  • [4] Synthesis and Antimicrobial, Analgesic, Antipyretic, and Immunotropic Activity of Methyl 3-Aryl-6-Amino-4-Aryl-5-Cyano-4H-Pyran-2-Carboxylates
    Mar'yasov, M. A.
    Davydova, V. V.
    Sheverdov, V. P.
    Nasakin, O. E.
    Gein, V. L.
    [J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2016, 50 (08) : 519 - 522
  • [5] Synthesis and Antimicrobial, Analgesic, Antipyretic, and Immunotropic Activity of Methyl 3-Aryl-6-Amino-4-Aryl-5-Cyano-4H-Pyran-2-Carboxylates
    M. A. Mar’yasov
    V. V. Davydova
    V. P. Sheverdov
    O. E. Nasakin
    V. L. Gein
    [J]. Pharmaceutical Chemistry Journal, 2016, 50 : 519 - 522
  • [6] Efficient one-pot synthesis of 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates catalyzed by nano MgO in water
    Sojoudi, Maryam
    Mokhtary, Masoud
    [J]. IRANIAN CHEMICAL COMMUNICATION, 2018, 6 (02) : 125 - 133
  • [7] Synthesis of 2-amino-4-aryl-3-cyano-6-methyl-5-ethoxycarbonyl-4H-pyrans
    Shestopalov, AM
    Niazimbetova, ZI
    Evans, DH
    Niyazymbetov, ME
    [J]. HETEROCYCLES, 1999, 51 (05) : 1101 - 1107
  • [8] Methyl 6-amino-5-cyano-2-methoxycarbonylmethyl-4-phenyl-4H-pyran-3-carboxylate
    Öztürk, S
    Akkurt, M
    Stoyanov, E
    Büyükgüngör, O
    Heber, D
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O283 - O284
  • [9] Ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate
    Li, YL
    Wang, XS
    Zeng, ZS
    Shi, DQ
    Wei, XY
    Zong, ZM
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1115 - O1117
  • [10] Ethyl 6-amino-5-cyano-2-methyl-4-propyl-4H-pyran-3-carboxylate
    Yu, Qun-Di
    Li, Ke-Xin
    Liu, Yun-Yu
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2862 - U1838