Synthesis and structural studies of (2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic acids

被引:0
|
作者
Dolzhenko, AV
Kolotova, NV
Kozminykh, VO
Chui, WK
Heng, PWS
Khrustalev, VN
机构
[1] Perm State Pharmaceut Acad, Perm 61499, Russia
[2] Natl Univ Singapore, Fac Sci, Dept Pharm, Singapore 117543, Singapore
[3] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
关键词
2-aminopyridine; imidazo[1,2-a[pyridine; NMR spectroscopy; X-ray crystallography; tautomerism;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2-Oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic acids (4a-c, 9a-c) were prepared from 2-aminopyridines by acylation with maleic or citraconic anhydrides and followed by Michael addition. Formation of 3-methyl substituted derivatives (9a-c) from citraconic anhydride was found to be regioselective. The molecular conformations of the products in the solution and in the crystal form were discussed based on H-1 NMR spectral and X-Ray data.
引用
收藏
页码:55 / +
页数:9
相关论文
共 50 条
  • [41] Synthesis and Structure of 2-(1De-Indol-1-yl)-6-ferrocenyl-4-(2-chloroimidazo[1,2-a]pyridin-3-yl)pyrimidine
    Antuf'eva, A. D.
    Akhmatzyanova, D. R.
    Dmitriev, M. V.
    Shklyaeva, E. V.
    Abashev, G. G.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (06) : 1103 - 1107
  • [42] Synthesis of Substituted Imidazo[1,2-a]Pyridin-3-yl-Acetic Acids by Multicomponent Condensation of 2-Aminopyridines with Arylglyoxals and Meldrum's Acid
    Lichitsky, Boris V.
    Tretyakov, Aleksander D.
    Komogortsev, Andrey N.
    Mityanov, Vitaly S.
    Dudinov, Arkady A.
    Krayushkin, Mikhail M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (02) : 156 - 159
  • [43] Influence of electronic and steric factors on 2,3-dihydroimidazo [1,2-a]pyridine-based enantioselective acylation catalysts
    Birman, VB
    Li, XM
    Jiang, H
    Uffman, EW
    TETRAHEDRON, 2006, 62 (2-3) : 285 - 294
  • [44] Double Hydroamination of Alkyne via PTC and Microwave-activated Diastereoselective Synthesis of 2,3-dihydroimidazo[1,2-a]pyridine in an Aqueous Media
    Waseem, Malik A.
    Lone, Ali Mohd
    Ibad, Farah
    Ibad, Afshan
    Yadav, Vijay B.
    Ansari, Khursheed
    Shairjogrey, Bashir Ahamad
    Watal, Geeta
    Siddiqui, I. R.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (05) : 2733 - 2739
  • [45] SYNTHESIS AND TRANSFORMATIONS OF 2,3-DIOXO-2,3-DIHYDROIMIDAZO-[1,2-A]BENZIMIDAZOLE DERIVATIVES
    SIMONOV, AM
    KOSHCHIENKO, YV
    SUVOROVA, GM
    TERTOV, BA
    MALYSHEVA, YN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1976, (10): : 1391 - 1395
  • [46] Synthesis of new (3-fluoroimidazo[1,2-a]pyridin-2-yl)-phosphonates
    Aksinenko, A. Yu.
    Goreva, T. V.
    Epishina, T. A.
    Sokolov, V. B.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (03) : 417 - 420
  • [47] Synthesis of new (3-fluoroimidazo[1,2-a]pyridin-2-yl)-phosphonates
    A. Yu. Aksinenko
    T. V. Goreva
    T. A. Epishina
    V. B. Sokolov
    Chemistry of Heterocyclic Compounds, 2013, 49 : 417 - 420
  • [48] Synthesis of 2-imino-7-methyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-ones and their reactions with nucleophiles
    Jakubkiene, Virginija
    Kacnova, Zana
    Burbuliene, Milda M.
    Vainilavicius, Povilas
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) : 1391 - 1395
  • [49] Investigations on substituted (2-aminothiazol-5-yl)(imidazo[1,2-a]pyridin-3-yl)methanones for the treatment of Alzheimer's disease
    Sagar, Sneha R.
    Singh, Devendra Pratap
    Das, Rajesh D.
    Panchal, Nirupa B.
    Sudarsanam, Vasudevan
    Nivsarkar, Manish
    Vasu, Kamala K.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 36
  • [50] Synthesis of Substituted 2-Oxo-2,3-dihydro-1H-imidazo-[1,2-a]indole-6,7-dicarbonitriles
    Chirkova, Zh. V.
    Kabanova, M. V.
    Makar'ina, T. G.
    Filimonov, S. I.
    Abramov, I. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (03) : 287 - 290