VILSMEIER REAGENT: AN EFFICIENT REAGENT FOR THE TRANSFORMATION OF 2-AMINOBENZAMIDES INTO QUINAZOLIN-4(3H)-ONE DERIVATIVES

被引:27
作者
Farzipour, Soghra [1 ]
Saeedi, Mina [2 ]
Mahdavi, Mohammad [2 ]
Yavari, Hossein [2 ]
Mirzahekmati, Mohammadreza [2 ]
Ghaemi, Nasser [1 ]
Foroumadi, Alireza [2 ]
Shafiee, Abbas [2 ]
机构
[1] Univ Tehran, Sch Chem, Coll Sci, Tehran, Iran
[2] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm & Pharmaceut Sci, Res Ctr, Tehran 14176, Iran
基金
美国国家科学基金会;
关键词
2-Aminobenzamides; heterocycles; isotoic anhydride; 4(3H)-quinazolinones; Vilsmeier reagent; PLATELET ANTIAGGREGANT ACTIVITY; SOLVENT-FREE CONDITIONS; IN-VITRO; CYCLIZATION; CONVENIENT; IODINE; AGENTS;
D O I
10.1080/00397911.2013.811528
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Clean and easy preparation of quinazolin-4(3H)-one derivatives using 2-aminobenzamides and Vilsmeier reagent is described. 2-Aminobenzamides were converted into the corresponding quinazolinones under mild and efficient conditions, in good yields without undesirable by-products. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
引用
收藏
页码:481 / 487
页数:7
相关论文
共 38 条
  • [1] [Anonymous], 1960, Angew. Chem.
  • [2] Photoinduced Elimination in 2,3-Dihydro-2-tert-butyl-3-benzyl-4(1H)-quinazolinone: Theoretical Calculations and Radical Trapping Using TEMPO Derivatives
    Araceli Cabrera-Rivera, Fanny
    Ortiz-Nava, Claudia
    Escalante, Jaime
    Hernandez-Perez, Julio M.
    Ho, Minhhuy
    [J]. SYNLETT, 2012, (07) : 1057 - 1063
  • [3] Reaction of Isatoic Anhydride, Amine, and N,N′-Dialkyl Carbodiimides Under Solvent-Free Conditions: New and Efficient Synthesis of 3-Alkyl-2-(alkylamino)quinazolin-4(3H)-ones
    Asadi, Mehdi
    Ebrahimi, Mostafa
    Mahdavi, Mohammad
    Saeedi, Mina
    Ranjbar, Parviz Rashidi
    Yazdani, Farshad
    Shafiee, Abbas
    Foroumadi, Alireza
    [J]. SYNTHETIC COMMUNICATIONS, 2013, 43 (17) : 2385 - 2392
  • [4] Baig G.U., 1984, J CHEM SOC P1, V1, P2765
  • [5] Cyclization of N-acylanthranilic acids with Vilsmeier reagents. Chemical and structural studies
    Bergman, J
    Stalhandske, C
    [J]. TETRAHEDRON, 1996, 52 (03) : 753 - 770
  • [6] Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains
    Cao, SL
    Feng, YP
    Jiang, YY
    Liu, SY
    Ding, GY
    Li, RT
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) : 1915 - 1917
  • [7] Selective synthesis of pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl) formamide, or N-(1H-pyrazol-5-yl)formamidine derivatives from N-1-substituted-5-aminopyrazoles with new Vilsmeier-type reagents
    Chang, Chun-Hsi
    Tsai, Henry J.
    Huang, Yu-Ying
    Lin, Hui-Yi
    Wang, Li-Ya
    Wu, Tian-Shung
    Wong, Fung Fuh
    [J]. TETRAHEDRON, 2013, 69 (04) : 1378 - 1386
  • [8] Recent progress in the synthesis of heterocyclic natural products by the Staudinger/intramolecular aza-Wittig reaction
    Eguchi, S
    [J]. ARKIVOC, 2005, : 98 - 119
  • [9] GRAVIER D, 1992, PHARMAZIE, V47, P91
  • [10] SYNTHESIS AND INVITRO STUDY OF PLATELET ANTIAGGREGANT ACTIVITY OF 1,2,3,4-TETRAHYDROQUINAZOLINE DERIVATIVES
    GRAVIER, D
    DUPIN, JP
    CASADEBAIG, F
    HOU, G
    BOISSEAU, M
    BERNARD, H
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1989, 24 (05) : 531 - 535