A new method for the construction of [1,2,4]triazolo[1,5-a]pyridine system

被引:2
|
作者
Kovtunenko, Volodymyr A. [1 ]
Potikha, Lyudmila M. [1 ]
Shelepyuk, Andriy V. [2 ]
Tarasiuk, Taras N. [1 ]
机构
[1] Kyiv Natl Taras Shevchenko Univ, 64 Volodymyrska St, UA-01033 Kiev, Ukraine
[2] Enamine Ltd, 78 Chervonotkatska St, UA-02660 Kiev, Ukraine
关键词
4-amino-4H-1,2,4-triazole; 1-amino-1H-[1; 2; 4]triazolo[1; 5-a]pyridine; -bromodipnone; 5-(bromomethyl)-2,2,6,6-tetramethylhept-4-en-3-one; deamination; quaternization; ONE-POT SYNTHESIS; RING;
D O I
10.1007/s10593-019-02466-w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quaternization of 4-amino-4H-1,2,4-triazole with -bromodipnones and 5-(bromomethyl)-2,2,6,6-tetramethylhept-4-en-3-one occurred at the N-1 nitrogen atom, with the formation of quaternary salts that were cyclized in the presence of bases into [1,2,4]triazolo[1,5-a]-pyridine derivatives. Quaternary 4-amino-4H-1,2,4-triazolium salts and aromatic 1-amino-1H-[1,2,4]triazolo[1,5-a]pyridinium salts can be deaminated by treatment with nitrous acid, giving 1-substituted 1,2,4-triazoles and the respective [1,2,4]triazolo[1,5-a]pyridines.
引用
收藏
页码:367 / 373
页数:7
相关论文
共 50 条
  • [41] Synthesis and Fungicidal Activities of New 1,2,4-Triazolo[1,5-a]pyrimidines
    Chen, Qiong
    Liu, Zu-Ming
    Chen, Chao-Nan
    Jiang, Li-Li
    Yang, Guang-Fu
    CHEMISTRY & BIODIVERSITY, 2009, 6 (08) : 1254 - 1265
  • [42] Addition of Hydrazine to 4,7-Dihydro[1,2,4]triazolo[1,5-a]pyrimidines: Hydrazine Derivatives of 4,5,6,7-Tetrahydro[1,2,4]triazolo[1,5-a]pyrimidine
    Komykhov, Sergey A.
    Ostras, Konstantin S.
    Kobzar, Kyryl M.
    Musatov, Vladimir I.
    Desenko, Sergey M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (06) : 1413 - 1415
  • [43] A FACILE SYNTHESIS OF 2-ARYL-[1,2,4]TRIAZOLO[1,5-A]BENZIMIDAZOLES
    REDDY, BS
    SAMBAIAH, T
    REDDY, KK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (03): : 191 - 192
  • [44] A general synthesis of furo[3,2-c][1,2,4]triazolo[1,5-a]azepine and furo [2,3-f][1,2,4]triazolo[1,5-a]azepine derivatives
    Meng, Qingqing
    Bai, Hexiang
    Wang, Quanrui
    Tao, Fenggang
    SYNTHESIS-STUTTGART, 2007, (01): : 33 - 38
  • [45] Synthesis and reactions of [1,2,4]triazolo[1,5-a]pyrimidinium-2-aminides
    Bishop, BC
    Marley, H
    Preston, PN
    Wright, SHB
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11): : 1527 - 1532
  • [46] 1,2,4-TRIAZOLO[1,5-A]BENZIMIDAZOLES - TAUTOMERISM AND ALKYLATION
    KUZMENKO, VV
    KUZMENKO, TA
    POZHARSKII, AF
    DORONKIN, VN
    CHIKINA, NL
    POZHARSKAYA, SS
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1989, (02): : 209 - 220
  • [47] A novel rearrangement to 1,2,4-triazolo[1,5-a]quinoxalines
    Katritzky, AR
    Huang, TB
    Denisko, OV
    Steel, PJ
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09): : 3118 - 3119
  • [48] Stable salts of 1,2,4-triazolo[1,5-a]pyrimidinium
    Kolos, NN
    Orlov, VD
    Paponov, BV
    Shishkin, OV
    Baumer, SV
    Kvashnitskaya, NA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1999, (06): : 796 - 804
  • [49] A new synthesis of 2-(aminoalkyl)-1,2,4-triazolo[1,5-a]pyrimidines
    Prezent, Mikhail A.
    Daeva, Elena D.
    Baranin, Sergey V.
    Zavarzin, Igor V.
    MENDELEEV COMMUNICATIONS, 2017, 27 (02) : 169 - 171
  • [50] On triazoles -: XLIV.: Synthesis of new ring systems containing imidazo[2′,1′:3,4][1,2,4]triazolo[1,5-a]pyrimidine and imidazo[1′,2′:2,3][1,2,4]triazolo[1,5-a]pyrimidine skeleton
    Berecz, G
    Reiter, J
    Argay, G
    Kálmán, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (02) : 319 - 325