Synthesis and transformations of N-butyl-3(5)-nitro-1,2,4-triazoles under the conditions of acid-catalyzed alkylation of 3(5)-nitro-1H-1,2,4-triazoles with butyl alcohols

被引:0
|
作者
Sukhanov, Gennady T. [1 ]
Krupnova, Irina A. [1 ]
Filippova, Yuliya, V [1 ]
Gatilov, Yurii, V [2 ]
Sukhanova, Anna G. [1 ]
Bosov, Konstantin K. [1 ]
Pivovarova, Ekaterina, V [1 ]
机构
[1] Russian Acad Sci, Inst Problems Chem & Energy Technol, Siberian Branch, 1 Sotsialisticheskaya St, Biisk 659322, Russia
[2] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
关键词
1-(tert-butyl)-4-(sec-butyl)-3-nitro-1,2,4-triazolium salt; 1-(sec-butyl)-3,5-dinitro-1H-1,2,4-triazole; N-(sec-butyl)-3(5)-nitro-1,2,4-triazole; alkylation; isomers; transformation of alkyl substituent; X-ray structural analysis; 5-SUBSTITUTED TETRAZOLES; 3-NITRO-1,2,4-TRIAZOLE; ADAMANTYLAZOLES; 1,2,4-TRIAZOLE; DERIVATIVES;
D O I
10.1007/s10593-020-02835-w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The directions of thermodynamically controlled rearrangements and transformations of alkyl substituents under the conditions of acidcatalyzed alkylation of unsubstituted and 5(3)-substituted 3(5)-nitro-1H-1,2,4-triazoles with butyl alcohols (n-, i-, tert-, sec-BuOH) were studied.
引用
收藏
页码:1440 / 1448
页数:9
相关论文
共 50 条
  • [41] NITROFURANYL HETEROCYCLES .13. N-METHYL-3-METHYLTHIO-5-(5-NITRO-2-FURANYL)-1H-1,2,4-TRIAZOLES
    BENJAMIN, LE
    SNYDER, HR
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (05) : 1115 - 1118
  • [42] Expanding the chemical space of 3(5)-functionalized 1,2,4-triazoles
    Khomenko, Dmytro M.
    Doroshchuk, Roman O.
    Ohorodnik, Yulia M.
    Ivanova, Hanna, V
    Zakharchenko, Borys, V
    Raspertova, Ilona, V
    Vaschenko, Oleksandr V.
    Dobrydnev, Alexey, V
    Grygorenko, Oleksandr O.
    Lampeka, Rostyslav D.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2022, 58 (2-3) : 116 - 128
  • [43] Reactions of 3-nitro-1,2,4-triazoles with alkylating agents. 6. Alkylation of a neutral heterocycle by alcohols in acid media
    Sukhanova, A. G.
    Sakovich, G. V.
    Sukhanov, G. T.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (11) : 1368 - 1373
  • [44] DEALKYLATION OF 1-ALKYL-3-NITRO-1,2,4-TRIAZOLES UNDER THE EFFECT OF POTASSIUM TERTIARY BUTYLATE
    TERPIGOREV, AN
    SHCHERBININ, MB
    BAZANOV, AG
    TSELINSKII, IV
    ZHURNAL ORGANICHESKOI KHIMII, 1982, 18 (03): : 676 - 677
  • [45] 1,2,4-TRIAZOLES .5. NUCLEAR MAGNETIC-RESONANCE STUDY OF N-METHYL DERIVATIVES OF 1,2,4-TRIAZOLES
    KUBOTA, S
    UDA, M
    NAKAGAWA, T
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (05) : 855 - 860
  • [46] ON TRIAZOLES .5. SYNTHESIS OF 1-R1-3-R2,R3-AMINO-5-AMINO-1,2,4-TRIAZOLES AND 2-R1-3-R2,R3-AMINO-5-AMINO-1,2,4-TRIAZOLES
    REITER, J
    PONGO, L
    SOMORAI, T
    DVORTSAK, P
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) : 401 - 408
  • [47] Trinitromethyl-Substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties
    Thottempudi, Venugopal
    Gao, Haixiang
    Shreeve, Jean'ne M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) : 6464 - 6471
  • [48] OXIDATIVE ALKYLATION OF AZOLES .1. INTERACTION OF N-CHLORO-3-NITRO-1,2,4-TRIAZOLES WITH METHYL-IODIDE
    PEVZNER, MS
    KURENKOV, AA
    TRUBITSIN, AE
    ZHURNAL ORGANICHESKOI KHIMII, 1994, 30 (09): : 1398 - 1403
  • [49] Tandem transformations of 1,2,4-triazol-5-ylidenes into 5-amidino-1,2,4-triazoles
    Korotkikh, Nikolai I.
    Glinyanaya, Nataliya V.
    Cowley, Alan H.
    Moore, Jennifer A.
    Knishevitsky, Arthur V.
    Pekhtereva, Tatyana M.
    Shvaika, Oles P.
    ARKIVOC, 2007, : 156 - 172
  • [50] Synthesis and in vitro antimicrobial evaluation of 5-(1-methyl-5-nitro-2-imidazolyl)-4H-1,2,4-triazoles
    Shafiee, A
    Sayadi, A
    Roozbahani, MH
    Foroumadi, A
    Kamal, F
    ARCHIV DER PHARMAZIE, 2002, 335 (10) : 495 - 499