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
  • [21] 6-ARYL-1 AND 7-ARYL-1,2,4-TRIAZOLO[4,3-B]-1,2,4-TRIAZINES, SYNTHESIS AND CHARACTERIZATION
    TRUST, RI
    ALBRIGHT, JD
    LOVELL, FM
    PERKINSON, NA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1978, 176 (SEP): : 121 - 121
  • [22] A Modified Synthesis of 6-Aryl-3-(6-R-pyridin-2-yl)-1,2,4-triazines
    Shabunina, O. V.
    Starnovskaya, E. S.
    Shtaits, Ya. K.
    Kopchuk, D. S.
    Kovalev, I. S.
    Zyryanov, G. V.
    Rusinov, V. L.
    Chupakhin, O. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (10) : 1576 - 1578
  • [23] CHEMISTRY OF 1,2,4-TRIAZINES .I. REACTION OF 1,2,4-TRIAZINES WITH 1-DIETHYLAMINOPROPYNE
    NEUNHOEF.H
    FRUHAUF, HW
    TETRAHEDRON LETTERS, 1969, (37) : 3151 - &
  • [24] INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES - SYNTHESIS OF CONDENSED PYRIMIDINES
    TAYLOR, EC
    PONT, JL
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19): : 4287 - 4292
  • [25] A Modified Synthesis of 6-Aryl-3-(6-R-pyridin-2-yl)-1,2,4-triazines
    O. V. Shabunina
    E. S. Starnovskaya
    Ya. K. Shtaits
    D. S. Kopchuk
    I. S. Kovalev
    G. V. Zyryanov
    V. L. Rusinov
    O. N. Chupakhin
    Russian Journal of Organic Chemistry, 2018, 54 : 1576 - 1578
  • [26] KETENAMINALS AS 1,3-DINUCLEOPHILES IN THE SYNTHESIS OF CONDENSED 1,4-DIAZINES AND 1,2,4-TRIAZINES
    ALEKSEEV, SG
    CHARUSHIN, VN
    CHUPAKHIN, ON
    GORDEEV, MF
    DOROKHOV, VA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (02): : 438 - 438
  • [27] MASS SPECTRA OF 1,2,4-TRIAZINES AND RELATED COMPOUNDS
    PALMER, MH
    PRESTON, PN
    STEVENS, MFG
    ORGANIC MASS SPECTROMETRY, 1971, 5 (09): : 1085 - &
  • [28] THE CHEMISTRY OF 1,2,4-TRIAZINES .14. SYNTHESIS AND REACTIONS OF 5-CHLORO-1,2,4-TRIAZINES
    NEUNHOEFFER, H
    REICHEL, D
    CULLMANN, B
    REHN, I
    LIEBIGS ANNALEN DER CHEMIE, 1990, (07): : 631 - 640
  • [29] UNCONDENSED 1,2,4-TRIAZINES .2. MECHANISTIC PATHWAY OF GRIGNARD REACTION ON 1,2,4-TRIAZINES
    ZAHER, HA
    IBRAHIM, YA
    SHERIF, O
    MOHAMMADY, R
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (06): : 559 - 561
  • [30] Acyclo C-nucleosides analogues of condensed 1,2,4-triazines
    ElSayed, H
    ElAshry, ESH
    Rashed, N
    Hamid, HA
    Ramadan, ES
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1997, 52 (07): : 873 - 882