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
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2019年 / 55卷 / 4-5期
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
  • [21] Biological activities of [1,2,4]triazolo[1,5-a]pyrimidines and analogs
    Sergio Pinheiro
    Erick M. C. Pinheiro
    Estela M. F. Muri
    Jaqueline C. Pessôa
    Mayara A. Cadorini
    Sandro J. Greco
    Medicinal Chemistry Research, 2020, 29 : 1751 - 1776
  • [22] Biological activities of [1,2,4]triazolo[1,5-a]pyrimidines and analogs
    Pinheiro, Sergio
    Pinheiro, Erick M. C.
    Muri, Estela M. F.
    Pessoa, Jaqueline C.
    Cadorini, Mayara A.
    Greco, Sandro J.
    MEDICINAL CHEMISTRY RESEARCH, 2020, 29 (10) : 1751 - 1776
  • [23] NEW HERBICIDAL DERIVATIVES OF 1,2,4-TRIAZOLO[1,5-A] PYRIMIDINE
    KLESCHICK, WA
    COSTALES, MJ
    DUNBAR, JE
    MEIKLE, RW
    MONTE, WT
    PEARSON, NR
    SNIDER, SW
    VINOGRADOFF, AP
    PESTICIDE SCIENCE, 1990, 29 (03): : 341 - 355
  • [24] Synthesis of [1,2,4]triazolo[1,5-a]quinazolines from 7-methyl-5-phenyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine
    Sidorenko, Dmitrii Yu.
    Orlov, Valerii D.
    MENDELEEV COMMUNICATIONS, 2010, 20 (03) : 170 - 171
  • [25] Utility of cyano acid hydrazide in heterocyclic chemistry: A new route for the synthesis of new 1,2,4-triazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]isoquinolines
    Haleem, A
    Hussein, M
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1998, 53 (04): : 488 - 494
  • [26] SYNTHESIS OF 2-ARYL-[1,2,4]TRIAZOLO[1,5-A]PYRAZINES
    SAMBAIAH, T
    REDDY, KK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (07): : 444 - 445
  • [27] SYNTHESIS OF 2-ARYL[1,2,4]TRIAZOLO[1,5-A]PYRAZINES
    SAMBAIAH, T
    REDDY, KK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 57 - MEDI
  • [28] SYNTHESIS OF 2-ARYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINES
    KAMALA, K
    RAO, PJ
    REDDY, KK
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) : 3791 - 3793
  • [29] Utility of cyano acid hydrazide in heterocyclic chemistry: A new route for the synthesis of new 1,2,4-triazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]isoquinolines
    Hussein, Abdel Haleem Mostafa
    Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1998, 53 (04): : 488 - 494
  • [30] SYNTHESIS AND CRYSTAL-STRUCTURE OF PIPERIDINIUM 2-ARYL[1,2,4]TRIAZOLO[1,5-A]PYRIDINIDES AND THEIR NEUTRALIZATION TO 2-ARYL[1,2,4]TRIAZOLO[1,5-A]PYRIDINES
    HADI, A
    MARTIN, N
    SEOANE, C
    SOTO, JL
    ALBERT, A
    CANO, F
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (05) : 1229 - 1235
12345