An efficient one-pot synthesis of pyrimido[2,1-b][1,3]thiazine derivatives by reaction of activated acetylenes, thiouracils, and isocyanides

被引：26
|
作者：
Baharfar, Robabeh [1 ]
Baghbanian, Seyed Meysam [1 ]
Vahdat, Seyed Mohammad [2 ]
机构：
[1] Univ Mazandaran, Dept Chem, Babol Sar, Iran
[2] Islamic Azad Univ, Ayatollah Amoli Branch, Dept Chem, Amol, Iran
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 45期
关键词：
Pyrimido[2,1-b][1,3]thiazines; Isocyanides; Activated acetylenes; Multicomponent reaction; PYRIMIDINE; ACIDS;
D O I：
10.1016/j.tetlet.2011.09.008
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactive 1:1 zwitterionic intermediate, formed by the addition of isocyanides to dialkyl acetylenedi-carboxylates, was trapped by thiouracils to yield a ketenimine intermediate, which cyclized and then rearranged to afford pyrimido[2,1-b][1,3]thiazines in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6018 / 6020
页数：3
相关论文
共 50 条
  • [21] One-pot three component isocyanide-based reaction: Synthesis of novel tetracyclic fused furo[2′,3′:4,5]pyrimido[2,1-b][1,3]benzothiazole
    Zangouei, Mahdieh
    Esmaeili, Abbas Ali
    Mague, Joel T.
    TETRAHEDRON, 2017, 73 (20) : 2894 - 2900
  • [22] One-pot synthesis of novel polysubstituted pyrazole and pyrrolo[2,1-b]benzothiazole derivatives
    Dawood, KM
    JOURNAL OF CHEMICAL RESEARCH, 1998, (03) : 128 - 129
  • [23] Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 4,5-diphenyl-1,3-dihydro-2H-imidazol-2-one.: One-pot synthesis of 5H-imidazo[2,1-b][1,3]oxazine derivatives
    Adib, M
    Ghanbary, K
    Mostofi, M
    Bijanzadeh, HR
    TETRAHEDRON, 2005, 61 (10) : 2645 - 2648
  • [24] One-Pot Synthesis of Benzimidazo[2,1-b]thiazoline Derivatives through an Addition/Cyclization/Oxidative Coupling Reaction
    Wang, Haofeng
    Wu, Xin
    Wang, Luyu
    Li, Erfei
    Li, Xiaoyu
    Tong, Tao
    Kang, Honglan
    Xie, Jianwu
    Shen, Guodong
    Lv, Xin
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11934 - 11941
  • [25] One-pot, catalyst-free synthesis of novel spiro[indole-3,4′-pyrano[2′,3′:4,5]pyrimido [2,1-b][1,3]benzothiazole] derivatives
    Zangouei, Mahdieh
    Esmaeili, Abbas Ali
    JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (11-12) : 646 - 652
  • [26] 6-Polyfluoroalkylated 2-thiouracils in the synthesis of pyrimido[2,1-b][1,3,5]thiadiazines by the double Mannich reaction
    Khudina, Ol'ga G.
    Ivanova, Anna E.
    Burgart, Yanina V.
    Saloutin, Victor I.
    Kravchenko, Marionella A.
    JOURNAL OF FLUORINE CHEMISTRY, 2013, 147 : 31 - 35
  • [27] 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
  • [28] An Efficient One-Pot Strategies for the Synthesis of [1,3] Oxazine Derivatives
    Sapkal, Suryakant B.
    Shelke, Kiran F.
    Shingate, Bapurao B.
    Shingare, Murlidhar S.
    JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2010, 54 (04): : 437 - 442
  • [29] One-pot synthesis of new benzo[4,5]imidazo[2,1-b]pyrimido[4,5-d][1,3] thiazine-2,4(3H)-dione and benzo[4,5]imidazo[2,1-b][1,3]thiazin-4-one derivatives as new anti-cancer components
    Batooie, Nasim
    Khodaei, Mohammad Mehdi
    Bahrami, Kiumars
    Miraghaee, Seyyed Shahram
    Hosseinzadeh, Nouraddin
    Sajadimajd, Soraya
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1271
  • [30] FEATURES OF (BENZO)IMIDAZO[2,1-B][1,3]THIAZINE MEZYLATES REACTION WITH NUCLEOPHILIC REAGENTS
    Slyvka, Nataliia
    Saliyeva, Lesya
    Litvinchuk, Mariia
    Shishkina, Svitlana
    Vovk, Mykhailo
    CHEMISTRY & CHEMICAL TECHNOLOGY, 2023, 17 (03): : 542 - 548
12345