General Synthesis of 1-Aryl-6-azaisocytosines and Their Utilization for the Preparation of Related Condensed 1,2,4-Triazines

被引：3
|
作者：
Zalesak, Frantisek [1 ]
Slouka, Jan [1 ]
Styskala, Jakub [1 ]
机构：
[1] Palacky Univ, Fac Sci, Dept Organ Chem, 17 Listopadu 1192-12, CZ-77146 Olomouc, Czech Republic
来源：
MOLECULES | 2019年 / 24卷 / 19期
关键词：
1-aryl-6-azaisocytosine; 1; 2; 4-triazine; condensed; fused azaisocytosines; cyclization of arylhydrazones; 1-ARYL-6-AZAURACILE; CYCLIZATION; ANALOGS;
D O I：
10.3390/molecules24193558
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A simple general synthesis of 1-aryl-6-azaisocytosine-5-carbonitriles 4 is described. This method is based on coupling diazonium salts with cyanoacetylcyanamide 2 and then cyclization of the formed 2-arylhydrazono-2-cyanoacetylcyanamides 3. The 6-azaisocytosines 4 were studied with respect to tautomeric equilibrium and the transformation of functional groups, and used in the synthesis of the condensed heterocyclic compounds: Purine isosteric imidazo[2,1-c]-[1,2,4]triazine 8 and the 1,2,4-triazino[2,3-a]quinazolines 9-12.
引用
收藏
页数：13
相关论文
共 50 条
  • [31] Reaction of lithium 2-arylethynides with 6-aryl-3-(2-pyridyl)-1,2,4-triazines as an access to 6-aryl-5-arylvinyl-3-(2-pyridyl)-1,2,4-triazines
    Khasanov, Albert F.
    Kopehuk, Dmitry S.
    Kovalev, Igor S.
    Taniya, Olga S.
    Zyryanov, Grigory V.
    Rusinov, Vladimir L.
    Chupakhin, Oleg N.
    MENDELEEV COMMUNICATIONS, 2015, 25 (05) : 332 - 333
  • [32] One-pot synthesis of 1,2,4-triazines
    Rostamizadeh, S
    Sadeghi, K
    SYNTHETIC COMMUNICATIONS, 2002, 32 (12) : 1899 - 1902
  • [33] Progress in the Synthesis of 1,2,4-Triazines by Tandem Cyclization
    Li, Mingrui
    Ding, Qifeng
    Li, Boyang
    Yu, Yang
    Huang, He
    Huang, Fei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (10) : 2713 - 2725
  • [34] SYNTHESIS OF 3-SUBSTITUTED 1,2,4-TRIAZINES
    YOKOYAMA, M
    TAKAHARU, E
    AIZAWA, Y
    KONNO, S
    YAMANAKA, H
    HETEROCYCLES, 1983, 20 (01) : 153 - 153
  • [35] SYNTHESIS OF ISOQUINOLINES BY CYCLOADDITION OF ARYNES TO 1,2,4-TRIAZINES
    GONSALVES, AMD
    MELO, TMVDPE
    GILCHRIST, TL
    TETRAHEDRON, 1992, 48 (33) : 6821 - 6826
  • [36] Synthesis and chemistry of fluorine containing bioactive 1,2,4-triazines - An overview - Chemistry of uncondensed 1,2,4-triazines, part III
    Abdel-Rahman, RM
    PHARMAZIE, 1999, 54 (11): : 791 - 803
  • [37] New possibilities of 1,2,4-triazines functionalization: first examples of synthesis and structure of boron-containing 1,2,4-triazines
    Azev, Y
    Lork, E
    Duelcks, T
    Gabel, D
    TETRAHEDRON LETTERS, 2004, 45 (16) : 3249 - 3252
  • [38] SYNTHESIS AND STRUCTURE OF 1-BENZOPYRANNO-1,2,4-TRIAZINES
    VINOT, N
    MAITTE, P
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (01) : 33 - 37
  • [39] Synthesis and Tuberculostatic Activity of Some 1,2,4-Triazines
    E. V. Shchegol’kov
    O. G. Khudina
    A. E. Ivanova
    Ya. V. Burgart
    E. V. Sadchikova
    M. A. Kravchenko
    V. I. Saloutin
    Pharmaceutical Chemistry Journal, 2014, 48 : 383 - 386
  • [40] Synthesis and Tuberculostatic Activity of Some 1,2,4-Triazines
    Shchegol'kov, E. V.
    Khudina, O. G.
    Ivanova, A. E.
    Burgart, Ya. V.
    Sadchikova, E. V.
    Kravchenko, M. A.
    Saloutin, V. I.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (06) : 383 - 386
12345