1-Methyl-8-phenyl-1,3-diazaspiro[4.5]decane-2,4-dione

被引:1
|
作者
Pardali, Vasiliki [1 ]
Katsamakas, Sotirios [1 ]
Giannakopoulou, Erofili [1 ]
Zoidis, Grigoris [1 ]
机构
[1] Natl & Kapodistrian Univ Athens, Sch Hlth Sci, Dept Pharm, Div Pharmaceut Chem, Athens 15771, Greece
关键词
carbocyclic hydantoins; N-1 substituted hydantoin; spiro hydantoins; imidazolidine-2,4-diones; DFT calculations; stereochemistry; NMR; HRMS; GIAO; ring closing; SPIN COUPLING-CONSTANTS; 2ND ROW ATOMS; BASIS-SET; PERTURBATION-THEORY; HYDANTOIN; ANTICONVULSANT; DERIVATIVES; INHIBITORS; ANALOGS; DESIGN;
D O I
10.3390/M1228
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, fast and cost-effective three-step synthesis of 1-methyl-8-phenyl-1,3-diazaspiro[4.5] decane-2,4-dione has been developed. The reactions described herein proceed readily, with high yields and no further purification. Therefore, the proposed method, with an overall yield of 60%, offers a facile pathway to the synthesis of N-1 monosubstituted spiro carbocyclic imidazolidine-2,4-diones (hydantoins), which constitute a privileged class of heterocyclic scaffolds with pharmacological interest.
引用
收藏
页数:7
相关论文
共 42 条
  • [1] Synthesis and structure–activity relationship studies on novel 8-amino-3-[2-(4-fluorophenoxy)ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione derivatives as anticonvulsant agents
    M. Madaiah
    M. K. Prashanth
    H. D. Revanasiddappa
    B. Veeresh
    Medicinal Chemistry Research, 2013, 22 : 2633 - 2644
  • [2] Synthesis and structure-activity relationship studies on novel 8-amino-3-[2-(4-fluorophenoxy)ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione derivatives as anticonvulsant agents
    Madaiah, M.
    Prashanth, M. K.
    Revanasiddappa, H. D.
    Veeresh, B.
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (06) : 2633 - 2644
  • [3] Palladium complexes with 3-methyl-8-thia-1,3-diaza-spiro[4.5]decane-2,4-dione: experimental and theoretical studies
    Cherneva, Emiliya D.
    Buyukliev, Rossen T.
    Bakalova, Adriana G.
    ARKIVOC, 2018, : 398 - 406
  • [4] Synthesis and Biological Evaluation of 1,3,8-Triazaspiro[4.5]decane-2,4-dione Derivatives as Myelostimulators
    Yu, Valentina
    Ten, Assel
    Baktybayeva, Lyailya
    Sagatbekova, Indira
    Praliyev, Kaldybay
    Zolotareva, Darya
    Seilkhanov, Tulegen
    Zazybin, Alexey
    JOURNAL OF CHEMISTRY, 2018, 2018
  • [5] Synthesis, Molecular Modeling, Anticonvulsant and Antinociceptive Properties of New 1,1-Disubstituted Cyclohexane and 1,3-Diazaspiro[4.5]decane Derivatives
    Aboul-Enein, Mohamed Nabil
    El-Azzouny, Aida A.
    Ragab, Fatma
    Abdel-Maksoud, Mohammed S.
    Abd-Allah, Walaa H.
    Maklad, Yousreya
    CHEMISTRYSELECT, 2019, 4 (04): : 1360 - 1365
  • [6] N-[3-(4-Fluorobenzyl)-2,4-dioxo-1,3-diazaspiro[4.5]dec-8-yl]-2-methylbenzenesulfonamide
    Jeyaseelan, S.
    Vinduvahini, M.
    Madaiah, M.
    Bhattacharya, Suman
    Revanasiddappa, H. D.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [7] Synthesis of 3-pentyl-5-(4-chlorobenzylidene)imidazolidine-2,4-dione and 1,3-dipentyl-5-(4-chlorobenzylidene)imidazolidine-2,4-dione
    Naufal, Muhammad
    Sabana, Irana Rahmawati
    Al-Anshori, Jamaludin
    Maharani, Rani
    Zainuddin, Achmad
    Sumiarsa, Dadan
    Hidayat, Ace Tatang
    Hidayat, Ika Wiani
    EGYPTIAN JOURNAL OF CHEMISTRY, 2022, 65 (12): : 95 - 99
  • [8] N-{3-[2-(4-Fluorophenoxy)ethyl]-2,4-dioxo-1,3-diazaspiro[4.5]decan-7-yl}-4-methoxybenzenesulfonamide
    Vinduvahini, M.
    Jeyaseelan, S.
    Shylajakumari, J.
    Revanasiddappa, H. D.
    Devaru, Venkatesh B.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [9] N-{3-[2-(4-Fluorophenoxy)ethyl]-2,4-dioxo-1,3-diazaspiro[4.5]decan-7-yl}-4-methylbenzamide
    Vinduvahini, M.
    Saha, Binoy Krishna
    Mahalakhmi
    Revanasiddappa, H. D.
    Devarajegowda, H. C.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1440 - U929
  • [10] Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study
    Lazic, Anita M.
    Bozic, Bojan D.
    Vitnik, Vesna D.
    Vitnik, Zeljko J.
    Rogan, Jelena R.
    Radovanovic, Lidija D.
    Valentic, Natasa V.
    Uscumlic, Gordana S.
    JOURNAL OF MOLECULAR STRUCTURE, 2017, 1127 : 88 - 98