New method for the synthesis of thieno[2,3-d]pyrimidines

被引：0
|
作者：
O. B. Ryabova
M. I. Evstratova
V. A. Makarov
V. A. Tafeenko
V. G. Granik
机构：
[1] State Antibiotics Research Center,
[2] M. V. Lomonosov Moscow State University,undefined
来源：
Chemistry of Heterocyclic Compounds | 2004年 / 40卷 / 10期
关键词：
isothiazolo[5,4-; ]pyrimidine; nitromethane; thieno[2,3-; ]pyrimidine; 5-formylpyrimidine;
D O I：
10.1007/s10593-005-0082-y
中图分类号：
学科分类号：
摘要：
The reaction of 5-formyl-4-thiocyanatopyrimidines with nitromethane was studied under various conditions. The reaction was found unexpectedly to proceed with closure of a thiophene ring to give thieno[2,3-d]pyrimidines. The use of ammonium acetate as the catalyst leads to a side reaction involving closure of an isothiazole ring to give isothiazolo[5,4-d]pyrimidines. X-ray diffraction crystallographic analysis was used to confirm the structure of thieno[2,3-d]pyrimidine.
引用
收藏
页码：1352 / 1358
页数：6
相关论文
共 50 条
  • [1] New method for the synthesis of thieno[2,3-d]pyrimidines
    O. B. Ryabova
    M. I. Evstratova
    V. A. Makarov
    V. A. Tafeenko
    V. G. Granik
    Chemistry of Heterocyclic Compounds, 2004, 40 (10) : 1352 - 1358
  • [2] SYNTHESIS OF THIOPYRANO[2,3-D]PYRIMIDINES AND THIENO[2,3-D]PYRIMIDINES
    ASSY, MG
    ELKAFRAWY, A
    HASSANIEN, MM
    POLISH JOURNAL OF CHEMISTRY, 1995, 69 (06) : 887 - 891
  • [3] SYNTHESIS OF THIOPYRANO [2,3-D]PYRIMIDINES AND THIENO [2,3-D]PYRIMIDINES
    SANTILLI, AA
    SCOTESE, AC
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (03) : 361 - 365
  • [4] SYNTHESIS OF 2-ARYLTHIOPYRANO[2,3-D]PYRIMIDINES AND THIENO[2,3-D]PYRIMIDINES
    ELBAHAIE, S
    ASSY, MG
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1990, 37 (05) : 497 - 500
  • [5] SYNTHESIS OF 2-ARYLTHIOPYRANO[2,3-D]PYRIMIDINES AND THIENO[2,3-D]PYRIMIDINES
    ASSY, MG
    HASSANIEN, MM
    ABDELRAHMAN, S
    PHARMAZIE, 1990, 45 (10): : 792 - 793
  • [6] Solid supported synthesis of new thieno[2,3-d]pyrimidines
    Green Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi-110007, India
    J. Sulfur Chem., 2006, 1 (57-63):
  • [7] Synthesis and Biological Activity of a Series of New Thieno[2,3-d]Pyrimidines
    Wang, Tao
    Zheng, Cai Hua
    Liu, Sue
    Chen, Hui Zong
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (07) : 1543 - 1549
  • [8] FURO-[2,3-D]PYRIMIDINES THIENO-[2,3-D]PYRIMIDINES AND PYRROLO[2,3-D]PYRIMIDINES
    MELIKOGANDZHANYAN, RG
    KHACHATRYAN, VE
    GAPOYAN, AS
    USPEKHI KHIMII, 1985, 54 (03) : 450 - 478
  • [9] Novel synthesis of thieno[2,3-c]pyrazoles and thieno[2,3-d]pyrimidines
    Ahluwalia, VK
    Dahiya, A
    Bala, M
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (07): : 715 - 717
  • [10] Synthesis of new thieno[2,3-d]pyrimidines, thieno[3,2-e]pyridines, and thieno[2,3-d][1,3]oxazines
    Kanawade, Shrikant B.
    Patil, Shivaraj P.
    Nikam, Prashant S.
    Gangurde, Sachin A.
    Jachak, Madhukar N.
    Toche, Raghunath B.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (02) : 363 - 369
12345