An efficient synthesis of novel pyridothieno-fused thiazolo[3,2-α]pyrimidinones via Pictet–Spengler reaction

被引:2
|
作者
Dao-Lin Wang [1 ]
Dong Wang [1 ]
Liang Yan [1 ]
Guang-Yu Pan [1 ]
Jian-Nan Yang [1 ]
机构
[1] College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound,Bohai University
关键词
7-Chloromethyl-5H-thiazolo[3,2-α]pyrimidin-5-one; 3-Cyanopyridine-2-thione; Pyrido[3’’,2’’,4’,5’]thieno[3’,2’,2,3]pyrido; 4,5:d] [1,3]Thiazolo[3,2-a]pyrimidine-4 one; Thorpe–Ziegler reaction; Pictet–Spengler reaction;
D O I
暂无
中图分类号
O626 [杂环化合物];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of novel pyrido[3’’,2’’:4’,5’]thieno[3’,2’:2,3]pyrido [4,5:d][1,3]thiazolo[3,2-a]pyrimidine-4-one derivatives(5) has been developed using a Pictet–Spengler reaction between 2-(3-aminothieno[2,3-b]pyridin-2-yl)thiazolo[3,2-a] pyrimidin-5-one(3), which could be obtained from the condensation of 7-(chloromethyl)-5H-thiazolo[3,2-a]pyrimidin-5-one(1) with3-cyanopyridine-2-thione(2) via Thorpe–Ziegler isomerization, and aromatic aldehydes under NHSOH as catalysis in good yields.
引用
收藏
页码:953 / 956
页数:4
相关论文
共 50 条
  • [41] An efficient diastereoselective synthesis of novel fused 5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones via one-pot three-component reaction
    Tabibi, Tooba
    Esmaeili, Abbas Ali
    Mague, Joel T.
    MOLECULAR DIVERSITY, 2022, 26 (01) : 183 - 190
  • [42] An efficient diastereoselective synthesis of novel fused 5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones via one-pot three-component reaction
    Tooba Tabibi
    Abbas Ali Esmaeili
    Joel T. Mague
    Molecular Diversity, 2022, 26 : 183 - 190
  • [43] Efficient Synthesis of Novel 1-Substituted β-Carboline Derivatives via Pictet-Spengler Cyclization of 5-Hydroxy-L-Tryptophan
    Ash'ari, Nur Ain Nabilah
    Pungot, Noor Hidayah
    Jani, Nor Akmalazura
    Shaameri, Zurina
    MALAYSIAN JOURNAL OF FUNDAMENTAL AND APPLIED SCIENCES, 2022, 18 (02): : 218 - 226
  • [44] Synthesis and biological evaluation of some novel fused thiazolo[3,2-a]pyrimidines as potential analgesic and anti-inflammatory agents
    Nagy M. Khalifa
    Mohamed A. Al-Omar
    Abd El-Galil E. Amr
    Ayman R. Baiuomy
    Rehab F. Abdel-Rahman
    Russian Journal of Bioorganic Chemistry, 2015, 41 : 192 - 200
  • [45] Synthesis and biological evaluation of some novel fused thiazolo[3,2-a]pyrimidines as potential analgesic and anti-inflammatory agents
    Khalifa, Nagy M.
    Al-Omar, Mohamed A.
    Amr, Abd El-Galil E.
    Baiuomy, Ayman R.
    Abdel-Rahman, Rehab F.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2015, 41 (02) : 192 - 200
  • [46] Access to Seleno-Functionalized Thiazolo[3,2-a]Pyrimidinones and Pyrimido[2,1-b][1,3]Thiazinones via Selenocyclization of 2-Alkenylthiopyrimidinones and Their Fused Analogs
    Vaskevych, Alla
    Shishkina, Svitlana
    Dekhtyar, Maryna
    Smolii, Oleg
    Vovk, Mykhailo
    CHEMISTRYSELECT, 2024, 9 (36):
  • [47] The first enantiospecific total synthesis of talcarpine 1 and talpinine 2 from D-(+)-tryptophan 3 via the asymmetric Pictet-Spengler reaction
    Yu, P
    Cook, JM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U53 - U53
  • [48] Diastereoselective synthesis of oxazolo[3,4-b] tetrahydroisoquinolin-3-ones via Lewis acid TMSOTf-mediated Pictet-Spengler reaction
    Zhang, Zhenbei
    Liu, Tong-Xin
    Liu, Qingfeng
    Zhang, Zhiguo
    Zhang, Guisheng
    TETRAHEDRON-ASYMMETRY, 2013, 24 (24) : 1591 - 1597
  • [49] CeCl3-Catalyzed a Highly Efficient and Eco-friendly Synthesis of New and Densely Functionalized Thiazolo[3,2-a]Pyrimidins via Biginelli-type Reaction
    Jazinizadeh, Tayebeh
    Yazdani-Elah-Abadi, Afshin
    Maghsoodlou, Malek Taher
    Heydari, Reza
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (03) : 732 - 742
  • [50] Skeletal Diverse Synthesis of N-Fused Polycyclic Heterocycles via the Sequence of Ugi-Type MCR and Cul-Catalyzed Coupling/Tandem Pictet-Spengler Reaction
    Tyagi, Vikas
    Khan, Shahnawaz
    Bajpai, Vikas
    Gauniyal, Harsh M.
    Kumar, Brijesh
    Chauhan, Prem M. S.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (03): : 1414 - 1421