FEATURES OF (BENZO)IMIDAZO[2,1-B][1,3]THIAZINE MEZYLATES REACTION WITH NUCLEOPHILIC REAGENTS

被引:0
|
作者
Slyvka, Nataliia [1 ]
Saliyeva, Lesya [1 ]
Litvinchuk, Mariia [2 ]
Shishkina, Svitlana [3 ]
Vovk, Mykhailo [2 ]
机构
[1] Lesya Ukrainka Volyn Natl Univ, Dept Organ Chem & Pharm, Volya Ave 13, UA-43025 Lutsk, Ukraine
[2] Natl Acad Sci Ukraine, Inst Organ Chem, Dept Funct Heterocycl Syst, Acad Kuharya St, UA-02660 Kiev, Ukraine
[3] Natl Acad Sci Ukraine, SSI Inst Single Crystals, Dept Xray Diffract Study & Quantum Chem, Nauka Ave 60, UA-61000 Kharkiv, Ukraine
来源
CHEMISTRY & CHEMICAL TECHNOLOGY | 2023年 / 17卷 / 03期
关键词
nucleo-philic substitution reaction; elimination reaction; thio (isothio)cyanato and azido derivatives; (benzo)imidazo[2,1-b][1,3]thiazines; ANALOGS;
D O I
10.23939/chcht17.03.542
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Peculiarities of the course of the methanesulfoderivatives of (benzo)imidazo[2,1-b][1,3]thiazines reactions with a number of nucleophilic reagents were studied. It was determined that they react nonselectively with potassium thiocyanate to form a mixture of thio-and isothiocyanate derivatives. When interacting with sodium azide, nucleophilic substitution competes with an elimina-tion reaction. The latter is dominant in the reaction with sodium cyanide. The spatial structure of one of the isomer elimination products, 4H-benzo[4,5]imidazo[2,1-b][1,3] thiazine, was established by X-ray structural analysis.
引用
收藏
页码:542 / 548
页数:7
相关论文
共 50 条
  • [1] Synthesis and Evaluation of Bioactivity of 6-[(2-Pyridinyloxy)] (Benzo)Imidazo[2,1-b] [1,3]Thiazine Derivatives
    Saliyeva, Lesya
    Slyvka, Nataliia
    Holota, Serhii
    Grozav, Alina
    Yakovychuk, Nina
    Litvinchuk, Mariia
    Vovk, Mykhailo
    BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2022, 12 (04): : 5031 - 5044
  • [2] New regioselective synthesis of 7H-imidazo[2,1-b][1,3]thiazine and 2H,6H-pyrimido[2,1-b][1,3]thiazine derivatives
    Landreau, Cyrille
    Deniaud, David
    Reliquet, Alain
    Meslin, Jean Claude
    Synthesis, 2002, (03) : 403 - 408
  • [3] New regioselective synthesis of 7H-imidazo[2,1-b][1,3]thiazine and 2H,6H-pyrimido[2,1-b][1,3]thiazine derivatives.
    Landreau, C
    Deniaud, D
    Reliquet, A
    Meslin, JC
    SYNTHESIS-STUTTGART, 2002, (03): : 403 - 408
  • [4] MESOIONIC NUCLEOSIDES .3. STUDIES ON MESOIONIC IMIDAZO[2,1-B]-1,3-THIAZINE DERIVATIVES
    GLENNON, RA
    TEJANI, SM
    NUCLEOSIDES & NUCLEOTIDES, 1984, 3 (04): : 389 - 399
  • [5] THE PREPARATION OF DERIVATIVES CONTAINING THE IMIDAZO[2,1-B]THIAZINE AND 1,2,4-TRIAZOLO[3,2-B][1,3]THIAZINE SYSTEMS
    CLAYTON, JP
    OHANLON, PJ
    KING, TJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (07): : 1352 - 1355
  • [6] Synthesis of 3-halogen derivatives of imidazo[2,1-b]- and benzimidazo[2,1-b][1,3]thiazines
    Kochergin, PM
    Bagry, AK
    Galenko, GF
    Kovpak, DV
    Aleksandrova, EV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (07): : 1004 - 1005
  • [7] Imidazo[2,1-b][1,3]thiazine Derivatives as Potential Modulators of Alpha-Synuclein Amyloid Aggregation
    Misiunaite, Indre
    Mikalauskaite, Kamile
    Paulauskaite, Martyna
    Snieckute, Ruta
    Smirnovas, Vytautas
    Brukstus, Algirdas
    Ziaunys, Mantas
    Zutaute, Ieva
    ACS CHEMICAL NEUROSCIENCE, 2024, 15 (24): : 4418 - 4430
  • [8] Synthesis of novel derivatives of (benz)imidazo[2,1-b]pyrimido[4,5-d][1,3] thiazine
    Akbarzadeh, Marzieh
    Bakavoli, Mehdi
    Eshghi, Hossein
    Shiri, Ali
    JOURNAL OF CHEMICAL RESEARCH, 2017, (12) : 730 - 733
  • [9] REACTIONS OF 1,3-THIAZINE-2,6-DITHIONES .1. SYNTHESES OF 2-DIALKYLAMINO-1,3-THIAZINE-6-THIONES, "IMIDAZO[2,1-B]PYRIMIDINE-5-THIONES, AND PYRIMIDO[2,1-B]PYRIMIDINE-, PYRIMIDO [2,1-B] [1,3]DIAZEPINE-, AND PYRIMIDO[2,1-B]BENZIMIDAZOLE-4-THIONES
    YAMAMOTO, T
    MURAOKA, M
    TAKESHIMA, T
    JOURNAL OF CHEMICAL RESEARCH-S, 1979, (11): : 384 - 385
  • [10] Activated nitriles in heterocyclic: Synthesis novel syntheses of imidazo[2,1-b]-1,3-thiazine derivatives
    El-Din, AAM
    Elsharabasy, SA
    Hassan, AY
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (02) : 407 - 412