A modified Biginelli reaction toward oxygen-bridged tetrahydropyrimidines fused with substituted 1,2,4-triazole ring

被引：0
|
作者：
Mustafa K. Gümüş
Nikolay Yu. Gorobets
Yuriy V. Sedash
Valentin A. Chebanov
Sergey M. Desenko
机构：
[1] Artvin Coruh University,Science
[2] SSI “Institute for Single Crystals” of National Academy of Sciences of Ukraine,Technology Research and Application Center
[3] V. N. Karazin Kharkiv National University,undefined
来源：
Chemistry of Heterocyclic Compounds | 2017年 / 53卷
关键词：
3-amino-1,2,4-triazole; benzoxadiazocine; oxygen-bridged structure; Biginelli reaction; cascade reaction; microwave-assisted synthesis; multicomponent reaction; reaction mechanism;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A microwave-assisted Biginelli-like three-component condensation using salicylic aldehyde derivatives, acetone, and 5-substituted 3-amino-1,2,4-triazoles instead of the urea component results in the formation of oxygen-bridged tetrahydrotriazolopyrimidine derivatives (11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocines) in good yields and high purity. A plausible reaction mechanism for this transformation is discussed in details using literature and experimental data.
引用
收藏
页码：1261 / 1267
页数：6
相关论文
共 50 条
  • [41] Unexpected alternative direction of a Biginelli-like multicomponent reaction with 3-amino-1,2,4-triazole as the urea component
    Gorobets, Nikolay Yu.
    Sedash, Yuriy V.
    Ostras, Konstantin S.
    Zaremba, Oleg V.
    Shishkina, Svetlana V.
    Baumer, Vyacheslav N.
    Shishkin, Oleg V.
    Kovalenko, Sergiy M.
    Desenko, Sergey M.
    Van der Eycken, Erik V.
    TETRAHEDRON LETTERS, 2010, 51 (16) : 2095 - 2098
  • [42] The First Example of a Regioselective Biginelli-Like Reaction Based on 3-Alkylthio-5-amino-1,2,4-triazole
    Chen, Qiong
    Jiang, Li-Li
    Chen, Chao-Nan
    Yang, Guang-Fu
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (02) : 139 - 148
  • [43] A heat-resistant explosive featuring an N,N′-ethylene bridged 1,2,4-1H-triazole fused ring
    Wang, Shaoqing
    Li, Congcong
    Li, Shaojia
    Yin, Hongquan
    Ma, Qing
    Chen, Fu-Xue
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (17) : 7562 - 7565
  • [44] Reaction of substituted benzyl isocyanates on 3-amino-1H-1,2,4-triazole:: Formation of substituted 3-amino-N2-benzyl-1H-1,2,4-triazole-1-carboxamides and their fungicidal activity
    Naik, SB
    Joshi, V
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 12 (02) : 109 - 112
  • [45] Synthesis of heteroaromatic 3,3′-bridged biscarbenes of the 1,2,4-triazole series and their properties
    Kiselyov, Artyom V.
    Korotkikh, Nikolai I.
    Cowley, Alan H.
    Moore, Jennifer A.
    Findlater, Michael A.
    Pekhtereva, Tatyana M.
    Shvaika, Oles P.
    ARKIVOC, 2008, : 329 - 342
  • [46] SYNTHESIS OF 3-VINYL-1-HYDROXYMETHYL-1,2,4-TRIAZOLE BY WITTIG REACTION
    BAZHENOV, DN
    PEVZNER, MS
    OSTROVSKII, VA
    GINDIN, VA
    SHCHERBININ, MB
    KIZHNYAEV, VN
    ZHURNAL ORGANICHESKOI KHIMII, 1994, 30 (05): : 791 - 792
  • [47] FUSED MESOIONIC HETEROCYCLES - SYNTHESIS OF 1,2,4-TRIAZOLO(4,3-B)-1,2,4-TRIAZOLE DERIVATIVES
    MOLINA, P
    LORENZO, A
    CLARAMUNT, RM
    ELGUERO, J
    TETRAHEDRON LETTERS, 1984, 25 (47) : 5427 - 5428
  • [48] Synthesis of some substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives
    E. R. Dilanyan
    T. R. Hovsepyan
    R. G. Melik-Ohanjanyan
    Chemistry of Heterocyclic Compounds, 2008, 44 : 1395 - 1397
  • [49] Synthesis of some substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives
    Dilanyan, E. R.
    Hovsepyan, T. R.
    Melik-Ohanjanyan, R. G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (11) : 1395 - 1397
  • [50] Antimicrobial activity of novel substituted 1,2,4-triazole and 1,3-thiazole derivatives
    Saffour, Sana
    AL-Sharabi, Amal A.
    Evren, Asaf Evrim
    Cankilic, Meral Yilmaz
    Yurttas, Leyla
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1295
12345