Anionic cascade recyclization of pyrazolo[5,1-c][1,2,4]triazines to pyrrolo[1,2-b][1,2,4]triazine and [1,2,4]triazino[2′,3′:1,5]pyrrolo [3,2-c]isoquinoline systems

被引：12
|
作者：
Ivanov, Sergey M. [1 ,2 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prospekt 47, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Miusskaya Ploshchad 9, Moscow 125047, Russia
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 42期
关键词：
1,2,4-triazine; Pyrazolo[5,1-c][1,2,4]triazine; Pyrrolo[1,2-b][1,2,4]triazine; Lithiation; X-ray diffraction; ELECTROPHILIC SUBSTITUTION; DERIVATIVES; TRIAZINES; NITROGEN;
D O I：
10.1016/j.tetlet.2020.152404
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The treatment of tert-butyl 2-(7-bromo-3-tert-butyl-8-R-4-oxopyrazolo[5,1-c][1,2,4]triazin-1(4H)-yl)acetates (R = CN, CO2Et, NO2) with alkyl lithiums in THF at low temperature led to rapid cascade reactions with the formation of tert-butyl 7-amino-3-tert-butyl-8-R-2-oxo-1,2-dihydropyrrolo[1,2-b][1,2,4]triazine-6-carboxylates in high yields. However, only an inert 1,2,4-triazinone was isolated in the case of R = Me. A tetracyclic [1,2,4]triazino[2',3':1,5]pyrrolo[3,2-c]isoquinoline derivative was also formed via recyclization of the appropriately functionalized substrate. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] SYNTHESIS AND PROPERTIES OF PYRAZOLO[3,2-C]BENZO-1,2,4-TRIAZINES AND PYRAZOLO[3,2-C]PYRIDO[4,3-E][1,2,4]TRIAZINES
    HAUPTMANN, S
    BLATTMANN, G
    SCHINDLER, W
    JOURNAL FUR PRAKTISCHE CHEMIE, 1976, 318 (05): : 835 - 842
  • [32] Synthesis of new pyrazolo[5,1-c][1,2,4]triazines with antifungal and antibiofilm activities
    Salah A. Al-Trawneh
    Shoroq A. Al-Dawdieh
    Nader S. Abutaleb
    Amer H. Tarawneh
    Ehab A. Salama
    Mustafa M. El-Abadelah
    Mohamed N. Seleem
    Chemical Papers, 2020, 74 : 1241 - 1252
  • [33] SYNTHESIS OF SUBSTITUTED, PARTIALLY HYDROGENATED [1,2,4]TRIAZINO[4,5-A]INDOLES AND PYRROLO[1,2-D][1,2,4]TRIAZINES
    BOTTCHER, H
    ARZT, B
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (07): : 518 - 519
  • [34] Synthesis of some novel pyrazolo[1,5-a]pyrimidine, 1,2,4-triazolo[1,5-a]pyrimidine, pyrido[2,3-d]pyrimidine, pyrazolo[5,1-c]-1,2,4-triazine and 1,2,4-triazolo[5,1-c]-1,2,4-triazine derivatives incorporating a thiazolo[3,2-a]benzimidazole moiety
    Abdel-Aziz, Hatem A.
    Hamdy, Nehal A.
    Farag, Ahmad M.
    Fakhr, Issa M. I.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (04) : 1033 - 1037
  • [35] SYNTHESIS OF SUBSTITUTED FURO[2',3'-4,5]PYRROLO[1,2-D][1,2,4]TRIAZOLO[3,4-F][1,2,4]TRIAZINES
    BOBOSIK, V
    KRUTOSIKOVA, A
    DANDAROVA, M
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1995, 60 (04) : 709 - 714
  • [36] Synthesis of substituted furo[2′,3′:4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines
    Krutosíková, A
    Dandárová, M
    CHEMICAL PAPERS, 1999, 53 (02) : 123 - 125
  • [37] Synthesis of new halo-substituted pyrazolo[5,1-c][1,2,4]triazines
    S. M. Ivanov
    L. M. Mironovich
    L. A. Rodinovskaya
    A. M. Shestopalov
    Russian Chemical Bulletin, 2017, 66 : 727 - 731
  • [38] Synthesis of new halo-substituted pyrazolo[5,1-c][1,2,4]triazines
    Ivanov, S. M.
    Mironovich, L. M.
    Rodinovskaya, L. A.
    Shestopalov, A. M.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (04) : 727 - 731
  • [39] Synthesis of new pyrazolo[5,1-c][1,2,4]triazines with antifungal and antibiofilm activities
    Al-Trawneh, Salah A.
    Al-Dawdieh, Shoroq A.
    Abutaleb, Nader S.
    Tarawneh, Amer H.
    Salama, Ehab A.
    El-Abadelah, Mustafa M.
    Seleem, Mohamed N.
    CHEMICAL PAPERS, 2020, 74 (04): : 1241 - 1252
  • [40] Efficient Synthesis of 3,7-Diaryl-1,4-dihydro[1,2,4]triazolo[5,1-c][1,2,4]triazines
    Aiwale, Sachin T.
    Dallavalle, Sabrina
    SYNTHESIS-STUTTGART, 2012, 44 (19): : 3055 - 3058
12345