An efficient synthesis of 1,3-disubstituted 5-diethoxyphosphoryluracils

被引:5
|
作者
Pieta, Marlena [1 ]
Kedzia, Jacek [1 ]
Janecki, Tomasz [1 ]
机构
[1] Lodz Univ Technol TUL, Inst Organ Chem, PL-90924 Lodz, Poland
关键词
5-Diethoxyphosphoryluracils; Diethoxyphosphorylacetamides; N; N-Dimethylformamide-dimethyl acetal; Phosgene; ANTI-HIV ACTIVITY; DERIVATIVES; 5-FLUOROURACIL; ANTI-HIV-1; DIALKYL; POTENT; ACID;
D O I
10.1016/j.tetlet.2015.02.094
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient three-step procedure for the synthesis of 1,3-disubstituted 5-diethoxyphosphoryluracils is presented. The starting 2-diethoxyphosphorylacetamides were subjected to dimethylaminomethylidenation using N,N-dimethylformamide-dimethyl acetal and the 3-dimethylamino-2-diethoxyphosphorylpropenamides obtained were transformed into N,N'-disubstituted 3-amino-2-diethoxyphosphorylpropenamides by treatment with various amines. Cyclization in the presence of phosgene led to an efficient formation of the title compounds. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1891 / 1893
页数:3
相关论文
共 50 条
  • [1] SYNTHESIS OF 1,3-DISUBSTITUTED AZULENES
    SACCO, GR
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1972, 17 (03): : 386 - &
  • [2] SYNTHESIS OF 1,3-DISUBSTITUTED DIAZOLIDINES
    LAMBERT, JB
    HUSELAND, DE
    WANG, GT
    SYNTHESIS-STUTTGART, 1986, (08): : 657 - 658
  • [3] SYNTHESIS OF 1,3-DISUBSTITUTED ADAMANTANES
    FISCHER, W
    GROB, CA
    KATAYAMA, H
    HELVETICA CHIMICA ACTA, 1976, 59 (06) : 1953 - 1962
  • [4] SYNTHESIS OF ISOMERICALLY PURE (E)-1,3-DISUBSTITUTED AND (Z)-1,3-DISUBSTITUTED 1,3-DIENES
    MULZER, J
    BRUNTRUP, G
    KUHL, U
    HARTZ, G
    CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (11): : 3453 - 3469
  • [5] SYNTHESIS AND CHARACTERIZATION OF 1,3-DISUBSTITUTED DECAMETHYLCYCLOHEXASILANES
    HENGGE, E
    EIBL, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 428 (03) : 335 - 343
  • [6] Synthesis of certain 1,3-disubstituted 5-(ω-mercaptoalkyl)isocyanurates
    Shulaeva, MM
    Fattakhov, SG
    Reznik, VS
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 1999, 69 (11) : 1827 - 1831
  • [7] A CONVENIENT SYNTHESIS OF 1,3-DISUBSTITUTED PYRROLES
    VOROBYOVA, SL
    MAGEDOV, IV
    TRAVEN, VF
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1991, (05): : 634 - 635
  • [8] SYNTHESIS OF 1,3-DISUBSTITUTED COBALTICINIUM SALTS
    MURR, NE
    DABARD, R
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 39 (02) : C82 - &
  • [9] SYNTHESIS OF 1-SUBSTITUTED AND 1,3-DISUBSTITUTED 5-HYDANTOINCARBOXYLATES
    LI, JP
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (23): : 3414 - 3417
  • [10] Facile benzannulation of isocoumarins in the efficient synthesis of diversified 1,3-disubstituted isoquinolines
    P. Manivel
    K. Prabakaran
    F. Nawaz Khan
    Jong Sung Jin
    Research on Chemical Intermediates, 2012, 38 : 347 - 357