4-(N-Boc-amino)-1H-1,2,3-triazolecarbothioamides in the synthesis of a new heterocyclic [1,2,3]triazolo[4,5-e][1,4]thiazepine system

被引：0
|
作者：
Syrota, Natalia A. [1 ]
Kemskiy, Sergiy, V [2 ]
Bol'but, Andriy, V [2 ,3 ]
Chernobaev, Igor I. [2 ]
Liavinets, Oleksandr S. [2 ]
Vovk, Mykhailo V. [2 ]
机构：
[1] Natl Univ Kyiv Mohyla Acad, 2 Hryhorija Skovorody St, UA-04655 Kiev, Ukraine
[2] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Murmanska St, UA-02660 Kiev, Ukraine
[3] Enamine Ltd, 78 Chervonotkatska St, UA-02094 Kiev, Ukraine
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2021年 / 57卷 / 7-8期
关键词：
4-(N-Boc-amino)-5-thioimidates; 4-(N-Boc-amino)-1H-1,2,3-triazolecarbothioamides; N-Boc-4-amino-1,2,3-triazoles; ethyl bromoacetate; 1,2,3]triazolo[1,4]thiazepines; ONE-POT SYNTHESIS; DERIVATIVES; ANTIOXIDANT;
D O I：
10.1007/s10593-021-02989-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4-(N-Boc-amino)-1H-1,2,3-triazolecarbothioamides, obtained by a sequential treatment of 4-(N-Boc-amino)-1H-1,2,3-triazoles with n-BuLi and alkyl isothiocyanates at -78 divided by-60 degrees C, reacted with ethyl bromoacetate, forming the respective 4-(N-Boc-amino)-5-thioimidates, which underwent intramolecular cyclocondensation upon treatment in saturated HCl solution in dioxane, producing 8-(alkylimino)-4,8-dihydro-1H-[1,2,3]triazolo[4,5-e][1,4]thiazepin-5(6H)-ones.
引用
收藏
页码：841 / 847
页数：7
相关论文
共 50 条
  • [31] Synthesis of 2Н-azolo[1,5-а][1,2,3]triazolo[4,5-е]pyrimidines
    Evgeny B. Gorbunov
    Gennady L. Rusinov
    Evgeny N. Ulomskii
    Maksim L. Isenov
    Valery N. Charushin
    Chemistry of Heterocyclic Compounds, 2015, 51 : 491 - 495
  • [32] Synthesis and density functional theory study of [1,2,3]triazolo[4,5-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives: A novel heterocyclic system
    Mozafari, Sarinasadat
    Shiri, Ali
    Bakavoli, Mehdi
    Akbarzadeh, Marzieh
    Saadat, Kayvan
    Etemadi, Yasaman
    JOURNAL OF CHEMICAL RESEARCH, 2016, (10) : 633 - 636
  • [33] HETEROCYCLIC CATION SYSTEMS .14. SYNTHESIS OF THIENO[3,2-E][1,4]DIAZEPINE, THIAZOLO[4,5-E][1,4]DIAZEPINE, AND S-TRIAZOLO[3,4-C]THIAZOLO[4,5-E][1,4]DIAZEPINE DERIVATIVES
    HIRAI, K
    SUGIMOTO, H
    ISHIBA, T
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (02): : 253 - 260
  • [34] Synthesis of 5-hydroxy- and 5-sulfanyl-substituted [1,2,3]triazolo[4,5-е][1,4]diazepines
    Sergiy V. Kemskiy
    Natalia A. Syrota
    Andriy V. Bol’but
    Viktor I. Dorokhov
    Mykhaylo V. Vovk
    Chemistry of Heterocyclic Compounds, 2018, 54 : 789 - 795
  • [35] 1-(FLUOROBENZYL)-4-AMINO-1H-1,2,3-TRIAZOLO[4,5-C]PYRIDINES - SYNTHESIS AND ANTICONVULSANT ACTIVITY
    KELLEY, JL
    KOBLE, CS
    DAVIS, RG
    MCLEAN, EW
    SOROKO, FE
    COOPER, BR
    JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (20) : 4131 - 4134
  • [36] SYNTHESIS OF NEW 1,2,3-TRIAZOLO-[4,5-D]PYRIDAZINE DERIVATIVES
    ANDERSEN, L
    NIELSEN, FE
    PEDERSEN, EB
    CHEMICA SCRIPTA, 1989, 29 (01): : 45 - 49
  • [37] Synthesis of the novel heterocyclic system 7,8-dihydroimidazo[1,2-c]-[1,3]oxazolo[4,5-e][1,2,3]triazine
    A. O. Gurenko
    O. V. Shablykin
    A. P. Kozachenko
    V. S. Brovarets
    Chemistry of Heterocyclic Compounds, 2012, 48 : 1423 - 1424
  • [38] Synthesis of 4-(1H-1,2,3-Triazol-4-YL)-1,3-Thiazole-2-Amine Derivatives
    Bunev, A. S.
    Trushkova, Yu. O.
    Ostapenko, G. I.
    Statsyuk, V. E.
    Peregudov, A. S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (07) : 1027 - 1031
  • [39] Synthesis of the novel heterocyclic system 7,8-dihydroimidazo[1,2-c]-[1,3]oxazolo[4,5-e][1,2,3]triazine
    Gurenko, A. O.
    Shablykin, O. V.
    Kozachenko, A. P.
    Brovarets, V. S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (09) : 1423 - 1424
  • [40] 4-{4-[(4-Oxoquinazolin-3-yl)methyl]-1H-1,2,3-triazol-1-yl}butyl acetate
    Ouahrouch, Abdelaaziz
    Taourirte, Moha
    Lazrek, Hassan B.
    El Azhari, Mohamed
    Saadi, Mohamed
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3191 - U1238
12345