An expeditious synthesis of pyrrolo[3,4-d]-pyrimidine-2,4-dione from uracil

被引:0
|
作者
Zimmerman, MN [1 ]
Nemeroff, NH [1 ]
Bock, CW [1 ]
Bhat, KL [1 ]
机构
[1] Philadelphia Univ, Sch Sci & Hlth, Dept Chem, Philadelphia, PA 19144 USA
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, practical and cost effective synthesis of the title compound has been realized from uracil. The key step is the construction of the pyrrole ring using tosylmethylisocyanide (TosMIC) methodology. The structure of uracil, reaction intermediates and the final product were investigated using density functional calculations.
引用
收藏
页码:205 / 211
页数:7
相关论文
共 50 条
  • [21] A complex of 5-hydroxypyrrolidin-2-one and pyrimidine-2,4-dione isolated from Jatropha curcas
    Staubmann, R
    Schubert-Zsilavecz, M
    Hiermann, A
    Kartnig, T
    PHYTOCHEMISTRY, 1999, 50 (02) : 337 - 338
  • [22] Synthesis and biological evaluation of pyrido[2,3-d]pyrimidine-2,4-dione derivatives as eEF-2K inhibitors
    Edupuganti, Ramakrishna
    Wang, Qiantao
    Tavares, Clint D. J.
    Chitjian, Catrina A.
    Bachman, James L.
    Ren, Pengyu
    Anslyn, Eric V.
    Dalby, Kevin N.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (17) : 4910 - 4916
  • [23] Pyrimidine-2,4-dione targets STAT3 signaling pathway to induce cytotoxicity in hepatocellular carcinoma cells
    Sajith, Ayyiliath M.
    Narasimhamurthy, Kereyagalahally H.
    Shanmugam, Muthu K.
    Rangappa, Shobith
    Nayak, S. Chandra
    Chinnathambi, Arunachalam
    Alahmadi, Tahani Awad
    Alharbi, Sulaiman Ali
    Haridas, K. R.
    Reddy, E. K.
    Savitha, B.
    Mohan, Chakrabhavi Dhananjaya
    Rangappa, Kanchugarakoppal S.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 50
  • [24] AZOLES .9. SYNTHESIS OF DERIVATIVES OF THIENO[2,3-D]THIAZOLE, 4H-PYRROLO-[2,3-D]THIAZOLE, 2H-PYRAZOLO[3,4-D]THIAZOLE AND ISOXAZOLO[3,4-D]THIAZOLE FROM THIAZOLIDINE-2,4-DIONE
    ATHMANI, S
    FARHAT, MF
    IDDON, B
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (08): : 973 - 977
  • [25] Atomistic Engineering of Chemiluminogens: Synthesis, Properties and Polymerization of 2,3-Dihydro-Pyrrolo[3,4-d]Pyridazine-1,4-Dione Scaffolds
    Melek Pamuk Algi
    Zahide Oztas
    Seha Tirkeş
    Atilla Cihaner
    Fatih Algi
    Journal of Fluorescence, 2017, 27 : 509 - 519
  • [26] Atomistic Engineering of Chemiluminogens: Synthesis, Properties and Polymerization of 2,3-Dihydro-Pyrrolo[3,4-d]Pyridazine-1,4-Dione Scaffolds
    Algi, Melek Pamuk
    Oztas, Zahide
    Tirkes, Seha
    Cihaner, Atilla
    Algi, Fatih
    JOURNAL OF FLUORESCENCE, 2017, 27 (02) : 509 - 519
  • [27] The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase
    Wang, Xiaowei
    Lou, Qinghua
    Guo, Ying
    Xu, Yang
    Zhang, Zhili
    Liu, Junyi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) : 3252 - 3258
  • [28] Synthesis and structure-activity relationships of thieno[2,3-d]pyrimidine-2,4-dione derivatives as potent GnRH receptor antagonists
    Guo, ZQ
    Chen, YS
    Wu, DP
    Zhu, YF
    Struthers, RS
    Saunders, J
    Me, Q
    Chen, C
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (20) : 3617 - 3622
  • [29] PYRROLOPYRIMIDINES .1. ELECTROPHILIC SUBSTITUTION-REACTIONS OF 1,3-DIMETHYLPYRROLO[3,2-D]PYRIMIDINE-2,4-DIONE
    TSUPAK, EB
    TKACHENKO, YN
    POZHARSKY, AF
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1994, (09): : 1242 - 1248
  • [30] SYNTHESIS OF ALKYL THIOETHERS OF PYRAZOLO[3,4-d]PYRIMIDINE
    Svalyavin, O. V.
    Onysko, M. Yu.
    Lendel, V. G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) : 827 - 828