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
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
  • [21] Syntheses of [1,2,3]selenadiazolo[4,5-e]benzofuran or benzothiophene, [1,2,3]thiadiazolo[4,5-e]benzofuran or benzothiophene, and 2-benzofuranyl-1,3,4-oxodiazole derivatives
    Shekarchi, M
    Ellahiyan, F
    Akbarzadeh, T
    Shafiee, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (03) : 427 - 433
  • [22] 1,2,3-TRIAZOLODIAZEPINES .1. PREPARATION AND BENZODIAZEPINE RECEPTOR-BINDING OF 1-BENZYL-1,2,3-TRIAZOLO-[4,5-B][1,4]DIAZEPINES AND 1-PHENETHYL-1,2,3-TRIAZOLO-[4,5-B][1,4]DIAZEPINES
    BIAGI, G
    GIORGI, I
    LIVI, O
    SCARTONI, V
    VELO, S
    LUCACCHINI, A
    SENATORE, G
    BARILI, PL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) : 169 - 176
  • [23] LEAD-TETRAACETATE OXIDATION OF 1-AMINO-5-PHENYL[1,2,3]TRIAZOLO[4,5-D][1,2,3]TRIAZOLES AND 2-AMINO-5-PHENYL[1,2,3]TRIAZOLO[4,5-D][1,2,3]TRIAZOLES - SYNTHESIS OF A FUSED 1,2,3,4-TETRAZINE
    KAIHOH, T
    ITOH, T
    YAMAGUCHI, K
    OHSAWA, A
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08): : 2045 - 2048
  • [24] STRUCTURE OF 2-PHENYL-1,2,3-TRIAZOLO(4,5-E)(1,2,3,4)TETRAZINE AT 153-K
    YAMAGUCHI, K
    KAIHOH, T
    ITOH, T
    OHSAWA, A
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 : 590 - 592
  • [25] Synthesis of a new heterocyclic system – pyrido[3',2':4,5]thieno- [2,3-e][1,2,3]triazolo[1,5-a]pyrimidine
    N. T. Pokhodylo
    V. S. Matiychuk
    N. D. Obushak
    Chemistry of Heterocyclic Compounds, 2009, 45 : 881 - 883
  • [26] SYNTHESIS OF A NEW HETEROCYCLIC SYSTEM - PYRIDO[3′,2′:4,5]THIENO-[2,3-e][1,2,3]TRIAZOLO[1,5-a]PYRIMIDINE
    Pokhodylo, N. T.
    Matiychuk, V. S.
    Obushak, N. D.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) : 881 - 883
  • [27] Synthesis and Characterization of Novel 2-(1,2,3-Triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles and 2-(4,5-Dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles
    Kariuki, Benson M.
    Abdel-Wahab, Bakr F.
    Mohamed, Hanan A.
    Bekheit, Mohamed S.
    El-Hiti, Gamal A.
    MOLECULES, 2022, 27 (24):
  • [28] Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamides
    Pingaew, Ratchanok
    Prachayasittikul, Supaluk
    Ruchirawat, Somsak
    Prachayasittikul, Virapong
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (04) : 1768 - 1780
  • [29] Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamides
    Ratchanok Pingaew
    Supaluk Prachayasittikul
    Somsak Ruchirawat
    Virapong Prachayasittikul
    Medicinal Chemistry Research, 2014, 23 : 1768 - 1780
  • [30] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF NEW HETEROCYCLIC STRUCTURES - [1,3]THIAZINO[2,3-I]PURINE, THIAZOLO[3,2-C] ]1,2,3]TRIAZOLO[4,5-E]PYRIMIDINE AND [1,2,3]TRIAZOLO [4', 5'/4,5] PYRIMIDO[6,1-B][1,3]THIAZINE
    RINALDI, M
    PECORARI, P
    COSTANTINO, L
    PROVVISIONATO, A
    MALAGOLI, M
    CERMELLI, C
    FARMACO, 1992, 47 (10): : 1315 - 1322