Citation: Dao-Lin Wang, Dong Wang, Liang Yan, Guang-Yu Pan, Jian-Nan Yang. An efficient synthesis of novel pyridothieno-fused thiazolo[3,2-a]pyrimidinones via Pictet–Spengler reaction[J]. Chinese Chemical Letters, ;2016, 27(6): 953-956. doi: 10.1016/j.cclet.2016.02.007 shu

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

College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou 121003, China

Received Date: 8 December 2015
Revised Date: 8 January 2016

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) with 3-cyanopyridine-2-thione (2) via Thorpe-Ziegler isomerization, and aromatic aldehydes under NH₂SO₃H as catalysis in good yields.
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
1. [1]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
2. [2]
  Mengzhao Liu , Jie Yin , Chengjian Wang , Weiji Wang , Yuan Gao , Mengxia Yan , Ping Geng . P doped Ni₃S₂ and Ni heterojunction bifunctional catalysts for electrocatalytic 5-hydroxymethylfurfural oxidation coupled hydrogen evolution reaction. Chinese Chemical Letters, 2025, 36(9): 111271-. doi: 10.1016/j.cclet.2025.111271
3. [3]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
4. [4]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
5. [5]
  Débora Ferreira dos Santos Morais , José Luis Tirado , Carlos Pérez-Vicente , Fabiana Villela da Motta , Pedro Lavela , Mauricio Bomio , Sergio Lavela . Unlocking the performance of sodium-ion batteries by coating Na₃V₂(PO₄)₃ with Nb₂O₅. Acta Physico-Chimica Sinica, 2026, 42(2): 100180-0. doi: 10.1016/j.actphy.2025.100180
6. [6]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
7. [7]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
8. [8]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
9. [9]
  Chenxi Shang , Boxuan Lu , Chongbei Wu , Shuqing Zhou , Luyan Shi , Tayirjan Taylor Isimjan , Xiulin Yang . Inducing electronic rearrangement through Co₃B-Mo₂B₅ catalysts: Efficient dual-function catalysis for NaBH₄ hydrolysis and 4-nitrophenol reduction. Chinese Chemical Letters, 2025, 36(9): 111152-. doi: 10.1016/j.cclet.2025.111152
10. [10]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108
11. [11]
  Jiawei Hu , Kai Xia , Ao Yang , Zhihao Zhang , Wen Xiao , Chao Liu , Qinfang Zhang . Interfacial Engineering of Ultrathin 2D/2D NiPS₃/C₃N₅ Heterojunctions for Boosting Photocatalytic H₂ Evolution. Acta Physico-Chimica Sinica, 2024, 40(5): 2305043-0. doi: 10.3866/PKU.WHXB202305043
12. [12]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
13. [13]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
14. [14]
  Yu Tian , Yijun Lin , Siyu Deng , Yinghe Tan , Xuanyi Bie , Zhaoyang Chen , Pangkuan Chen . Metal-Coordinate Complexes (M = 3d, 4f) with Enhanced Circularly Polarized Luminescence in Planar Chiral Pillar[5]arenes. Chinese Journal of Structural Chemistry, 2025, 44(8): 100626-100626. doi: 10.1016/j.cjsc.2025.100626
15. [15]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
16. [16]
  Xiaodong Zhang , Bohui Xu , Deshuai Xiao , Xinyuan Zhang , Pifu Gong , Zheshuai Lin . From centrosymmetric CN3H6C6H5SO3 to non-centrosymmetric CN3H6C6H4SO3(OH): Hydroxyl introduced hydrogen bond reconstruction to realize strong second harmonic generation. Chinese Journal of Structural Chemistry, 2025, 44(10): 100707-100707. doi: 10.1016/j.cjsc.2025.100707
17. [17]
  Ruixin XU , Hongtuo LI , Chen SHI , Yanhong YAN . Factors influencing the spectral properties of composite luminescent materials SrTiO₃: Eu³⁺/SrAl₂O₄: Eu²⁺, Dy³⁺. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2307-2316. doi: 10.11862/CJIC.20250055
18. [18]
  Yi-Chang Yang , Rui-Xi Wang , Li-Ming Wu , Ling Chen . Regulating the coplanarity of π-conjugated units through hydrogen bonding in FAHC2O4 and FAH2C3N3S3 crystals. Chinese Journal of Structural Chemistry, 2025, 44(10): 100714-100714. doi: 10.1016/j.cjsc.2025.100714
19. [19]
  Zhenguo Zhang , Lanyang Li , Xinlong Zong , Yongheng Lv , Shuanglei Liu , Liang Ji , Xuefei Zhao , Zhenhua Jia , Teck-Peng Loh . "Water" accelerated B(C₆F₅)₃-catalyzed Mukaiyama-aldol reaction: Outer-sphere activation model. Chinese Chemical Letters, 2025, 36(7): 110504-. doi: 10.1016/j.cclet.2024.110504
20. [20]
  Qiong-Hui Peng , Ning-Bo Li , Jia-Cheng Hou , Cai-Jun He , Ya-Xin Yang , Chun-Lin Zhuang , Li-Juan Ou , Mei Yuan , Wei-Min He . Nd@g-C₃N₄ dual-functional photosynthesis and antitumor activities of 3-fluoroalkylated quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2025, 36(12): 111402-. doi: 10.1016/j.cclet.2025.111402

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1226)
HTML views(28)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142