Promising approach to the synthesis of unknown 2-(2, 2′-diamino-4,5′-dipyrimidin-6-yl)phenols(naphthols) and 2-amino-6-(2-hydroxyphenyl)-4-(4-nitrophenyl)nicotinonitriles

被引:0
|
作者
Zahorulko, Serhii P. [1 ]
Varenichenko, Svetlana A. [1 ]
Farat, Oleg K. [1 ]
Mazepa, Aleksander V. [2 ]
Markov, Victor I. [1 ]
机构
[1] Ukrainian State Univ Chem Technol, 8 Gagarina Ave, Dnipro 49005, Ukraine
[2] Natl Acad Sci Ukraine, AV Bogatsky Physicochem Inst, 86 Lyustdorfskaya Rd, Odessa 65080, Ukraine
来源
MONATSHEFTE FUR CHEMIE | 2021年 / 152卷 / 01期
关键词
(4-Amino-2H-chromen-2-ylidene) malonaldehyde; 2-Aryl-4H-chromen-4-imines; Dipyrimidin-6-yl-phenols (naphthols); 2-Amino-6-(2-hydroxyphenyl)-4-(4-nitrophenyl) nicotinonitrile; 6-Exo-trig-cyclization; DINUCLEOPHILES; RECYCLIZATION; CLEAVAGE;
D O I
10.1007/s00706-020-02719-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel derivatives of 2-(2,2 '-diamino-4,5 '-bipyrimidin-6-yl)phenols(naphthols) were obtained in the reaction of (4-amino-2H-(benzo[g])chromen-2-ylidene)malondialdehyde with 1,3-dinucleophile proceeding as a cascade reaction initiated by the Michael reaction. It has been established that the recyclization of 2-aryl-4H-chromen-4-imines under the influence of malononitrile as C-nucleophile is completed by the formation of 2-amino-6-(2-hydroxyphenyl)-4-(4-nitrophenyl)nicotinonitrile by the 6-exo-trig-cyclization mechanism.
引用
收藏
页码:77 / 82
页数:6
相关论文
共 50 条
  • [41] Synthesis and reactions of 2-amino-6-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-4-phenylpyridine-3-carbonitrile
    Ahmed, RA
    Kandeel, MM
    Abbady, MS
    Youssef, MSK
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (02) : 309 - 314
  • [42] SYNTHESIS AND CRYSTAL STRUCTURE OF (E)-2-(2-HYDROXYPHENYL)-3-((1-(2-HYDROXYPHENYL)ETHYLIDENE)AMINO)-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE
    Mondal, B.
    JOURNAL OF STRUCTURAL CHEMISTRY, 2024, 65 (05) : 920 - 928
  • [43] Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-methoxypyrimidine-4-carboxylate
    Shang, Zhenhua
    Qi, Shan
    Tao, Xiao
    Zhang, Guangbo
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1335 - U2104
  • [44] Synthesis and some reactions of ethyl 4-(2,3-diphenyl-5-methoxybenzofuran-6-yl)- and 4-(2,3-diphenyl-6-methoxybenzofuran-5-yl)-2,4-diketobutanoates
    El-Rahman, AHA
    Kandeel, EM
    El-Sohibani, HA
    CHEMICAL PAPERS-CHEMICKE ZVESTI, 1998, 52 (01): : 41 - 44
  • [45] 2-amino-6-(1,2,4-triazol-4-yl)-purine: a useful intermediate in the synthesis of 9-alkylguanines
    Alarcon, K
    Martelli, A
    Demeunynck, M
    Lhomme, J
    TETRAHEDRON LETTERS, 2000, 41 (37) : 7211 - 7215
  • [46] 4,5,6,7-Tetrafluoro-2-(2-hydroxyphenyl)-isoindoline-1,3-dione
    Wang, Shou-Xin
    Tian, Lai-Jin
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4382 - U4007
  • [47] 6-(2-hydroxybenzoyl)-2-(4-nitrophenyl)pyrazolo-[1,5-a]pyrimidine
    Cannon, D
    Quesada, A
    Quiroga, J
    Insuasty, B
    Abonia, R
    Mejía, D
    Cobo, J
    Nogueras, M
    Sánchez, A
    Low, JN
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2001, 57 : o182 - o184
  • [48] 2-[(2,4,4,6,6-Pentachloro-1,3,5,2λ5,4λ5,6λ5-triazatriphosphinin-2-yl)azanidyl]pyridinium
    Ahmed, Safaa A.
    Haque, Rosenani A.
    Zetty, Zulikha H.
    Fun, Hoong-Kun
    Loh, Wan-Sin
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O306 - U1873
  • [49] Multicomponent synthesis of 2-(alkylsulfanyl)-4-[furan-2-yl-(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles
    V. D. Dyachenko
    V. N. Nesterov
    S. V. Dyachenko
    A. V. Chernykh
    Russian Journal of Organic Chemistry, 2015, 51 : 864 - 868
  • [50] Multicomponent synthesis of 2-(alkylsulfanyl)-4-[furan-2-yl-(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles
    Dyachenko, V. D.
    Nesterov, V. N.
    Dyachenko, S. V.
    Chernykh, A. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (06) : 864 - 868