Synthesis of 6-hydrazino-3,4-dimethyl-1H-pyrazolo[3,4-d]pyrimidine and its application for the construction of a pyrazolo[4,3-e][1,2,4]triazolo[4,3-a]pyrimidine system

被引:0
|
作者
A. V. Komkov
A. S. Shashkov
S. V. Baranin
V. A. Dorokhov
机构
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源
Russian Chemical Bulletin | 2013年 / 62卷
关键词
diacetyl ketene ; ,; -acetal; 5-acetyl-6-methyl-2,4-di(methylsulfanyl)pyrimidine; hydrazine; 6-hydrazino-1; -pyrazolo[3,4-; ]pyrimidine; amide acetals; aldehydes; condensation; oxidative cyclization; pyrazolo[4,3-; ][1,2,4]triazolo[4,3-; ]pyrimidines; 6-(1; -pyrazol-1-yl)-1; -pyrazolo[3,4-; ]pyrimidines;
D O I
暂无
中图分类号
学科分类号
摘要
A new representative of heterocyclic hydrazines, viz., 6-hydrazino-3,4-dimethyl-1H-pyrazolo[3,4-d]pyrimidine (3) was synthesized from diacetyl ketene N,S-acetal. A condensation of hydrazine 3 with amide acetals or aldehydes and subsequent cyclization furnished pyrazolo[4,3-e][1,2,4]triazolo[4,3-a]pyrimidines, whose structure was confirmed by 1H, 13C, and 1H/15N HMBC NMR spectroscopy. Reactions of hydrazine 3 with acetylacetone, ethyl acetoacetate, diethyl malonate, and acetic anhydride were studied.
引用
收藏
页码:1248 / 1254
页数:6
相关论文
共 50 条
  • [21] Alternative Routes to the Pyrazolo[4,3-e][1,2,4]triazolo-[1,5-c]pyrimidine System
    R. V. Tyurin
    E. V. Vorob’ev
    L. G. Minyaeva
    V. V. Krasnikov
    V. V. Mezheritskii
    Russian Journal of Organic Chemistry, 2005, 41 : 916 - 921
  • [22] Two approaches to a new heterocyclic system of pyrazolo[4,3-e][1,2,4] triazolo[1,5-c]pyrimidine
    Mezheritsky, Valery V.
    Minkin, Vladimir I.
    Minyaeva, Lyudmila G.
    Tyurin, Roman G.
    Krasnikov, Valery V.
    Vorobyev, Eugeny V.
    Starikova, Zoya A.
    ARKIVOC, 2005, : 9 - 17
  • [23] Synthesis and Biological Activity of Novel Thieno [2,3-d] [1,2,4] triazolo [4,3-a] pyrimidine and Pyrazolo [3,4-c] pyrazole Derivatives
    Mahran, Asma M.
    Abu-Zied, Khadiga M.
    Gad, Wafaa A.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2012, 55 (02): : 191 - 200
  • [24] 4-Benzylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine
    El Fal, Mohammed
    Ramli, Youssef
    Essassi, El Mokhtar
    Saadi, Mohamed
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1650 - +
  • [25] STUDIES ON PYRAZOLO[3,4-D]PYRIMIDINE DERIVATIVES .4. ON 1-METHYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE AND 1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE 5-OXIDE
    HIGASHINO, T
    IWAI, Y
    HAYASHI, E
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1976, 24 (12) : 3120 - 3134
  • [26] Synthesis of novel heterocycle systems: 6,8-dimethyl-2-(methylsulfanyl)-4-amino-substituted pyrimido[4′,5′:3,4]pyrazolo[1,5-a]pyrimidine and 9,11-dimethyl-5-(methylsulfanyl)pyrimido[2′,1′:5,1]pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidine
    Hasanpour, Maede
    Eshghi, Hossein
    Bakavoli, Mehdi
    Yusefi, Mozhdeh
    JOURNAL OF CHEMICAL RESEARCH, 2014, (11) : 643 - 647
  • [27] Synthesis of Novel Pyrazolo[3,4-d]pyridazine, Pyrido[1,2-a]benzimidazole, Pyrimido[1,2-a]benzimidazole and Triazolo[4,3-a]Pyrimidine Derivatives
    Shaaban, Mohamed R.
    Eldebss, Taha M. A.
    Darweesh, Ahmed F.
    Farag, Ahmad M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (06) : 1739 - 1744
  • [28] Pyrazolo [4,3-e][1,2,4]triazolo[1,5-c]pyrimidine template:: Organic and medicinal chemistry approach
    Baraldi, PG
    Tabrizi, MA
    Romagnoli, R
    El-Kashef, H
    Preti, D
    Bovero, A
    Fruttarolo, F
    Gordaliza, M
    Borea, PA
    CURRENT ORGANIC CHEMISTRY, 2006, 10 (03) : 259 - 275
  • [29] NITRILES IN HETEROCYCLIC SYNTHESIS - SYNTHESIS OF PYRAZOLO[1,5-A]PYRIMIDINE, PYRAZOLO[1,5-C][1,2,4]TRIAZINE AND PYRAZOLO[4,3-E][1,2,4]TRIAZINE DERIVATIVES
    ELAGAMEY, AGA
    MOHAMED, F
    ELTAWEEL, AA
    JOURNAL FUR PRAKTISCHE CHEMIE, 1991, 333 (02): : 333 - 338
  • [30] STUDIES ON PYRAZOLO[3,4-D]PYRIMIDINE DERIVATIVES .11. 1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE-4-CARBONITRILE
    HAYASHI, E
    HIGASHINO, T
    SUZUKI, S
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1978, 98 (07): : 891 - 897