Synthesis of new derivatives of 2,3-dicyano-imidazo [1,2-a] pyrimidine from 4-hydroxy-6-methylpyran-2-ones

被引：4
|
作者：
El Otmani, Bouchaib [1 ]
El Mahi, Mohammed [1 ]
Bouhfid, Rachid [1 ]
Essassi, El Mokhtar [1 ]
Rohand, Taoufik [2 ]
Dehaen, Wim [2 ]
El Ammari, Lahcen [3 ]
机构：
[1] Fac Sci Rabat, Lab Chim Organ Heterocycle, Rabat, Morocco
[2] Katholieke Univ Leuven, Dept Chem, B-3001 Heverlee, Belgium
[3] Fac Sci Rabat, Lab Chim Solid, Rabat, Morocco
来源：
ARKIVOC | 2008年
关键词：
2-amino-4,5-dicyanoimidazole; 4-hydroxy-6-methylpyran-2-one; 3-acetyl-4-hydroxy-6-methylpyran-2-one; imidazo[1,2-a]pyrimidines; o-phenylenediamines; benzimidazoles;
D O I：
10.3998/ark.5550190.0009.208
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactions of 2-amino-4,5-dicyanoimidazole 1 with lactone 2 in refluxing alcohol has been carried out for the first time and afforded imidazo[1,2-a] pyrimidines 4 and 5a-d. Condensation of compound 1 with 3-acetyl-4-hydroxy-6-methylpyran-2-one in refluxing n-butanol afforded bis(imidazopyrimidine) derivative 6. Reaction of hydrazine hydrate with ester 5 yielded the corresponding hydrazides 8. Condensation of o-phenylenediamines 9 with compound 5 in refluxing xylene or with hydrazides by melting reagents afforded 2,3-dicyano-5-[benzimidazol-2-yl]methyl-7-methylimidazo[1,2-a] pyrimidines 10a-d.
引用
收藏
页码：59 / 70
页数：12
相关论文
共 50 条
  • [41] Cu-Pybox catalyzed synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and propargyl alcohol derivatives
    Cheng, Cang
    Ge, Luo
    Lu, Xuehe
    Huang, Jianping
    Huang, Haocheng
    Chen, Jie
    Cao, Weiguo
    Wu, Xiaoyu
    TETRAHEDRON, 2016, 72 (43) : 6866 - 6874
  • [42] Synthesis, Pharmacological Activity and Molecular Modeling of 1-Aryl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidine-5(1H)-ones and their 6-Substituted Derivatives
    Rzadkowska, Marzena
    Szacon, Elzbieta
    Kaczor, Agnieszka A.
    Fidecka, Sylwia
    Kedzierska, Ewa
    Matosiuk, Dariusz
    MEDICINAL CHEMISTRY, 2014, 10 (05) : 460 - 475
  • [43] Reactions of pyrimidinonethione derivatives: Synthesis of 2-hydrazinopyrimidin-4-one, pyrimido[1,2-a]-1,2,4-triazine, triazolo-[1,2-a]pyrimidine, 2-(1-pyrazolo)pyrimidine and 2-arylhydrazonopyrimidine derivatives
    Attaby, FA
    Eldin, SM
    Hanafi, EAZ
    ARCHIVES OF PHARMACAL RESEARCH, 1997, 20 (06) : 620 - 628
  • [44] Synthesis and Biological Evaluation of New imidazo[1,2-a]pyridine Derivatives as Selective COX-2 Inhibitors
    Movahed, Mahsa Azami
    Daraei, Bahram
    Zarghi, Afshin
    LETTERS IN DRUG DESIGN & DISCOVERY, 2016, 13 (08) : 793 - 799
  • [45] An efficient synthesis of new imidazo[1,2-a]pyridine-6-carbohydrazide and pyrido[1,2-a]pyrimidine-7-carbohydrazide derivatives via a five-component cascade reaction
    Hosseini, Hajar
    Bayat, Mohammad
    RSC ADVANCES, 2019, 9 (13) : 7218 - 7227
  • [46] Reactions of pyrimidinonethione derivatives: Synthesis of 2-hydrazinopyrimidin-4-one, pyrimido[1,2-a]-1,2,4-triazine, triazolo-[1,2-a]pyrimidine, 2-(1-pyrazolo)pyrimidine and 2-arylhydrazonopyrimidine derivatives
    Fawzy A. Attaby
    Sanaa M. Eldin
    Eman A. Z. Hanafi
    Archives of Pharmacal Research, 1997, 20 : 620 - 628
  • [47] STEREOCHEMICAL STUDIES .62. POLAROGRAPHY OF 2,3-CYCLOALKYLENE-4H-PYRIDO[1,2-A] PYRIMIDINE-4-ONES
    PFLEGEL, P
    KUHMSTEDT, C
    FULOP, F
    BERNATH, G
    PHARMAZIE, 1984, 39 (02): : 106 - 109
  • [48] SYNTHESIS OF SOME 7-PHENYLPYRROLO[1,2-A]PYRIMIDINE DERIVATIVES .2.
    VETTORI, LP
    AUZZI, G
    BRUNI, F
    COSTANZO, A
    MELANI, F
    FARMACO-EDIZIONE SCIENTIFICA, 1987, 42 (10): : 717 - 725
  • [49] Research in the field of imidazo[1,2-a]benzimidazole derivatives. XXX. Synthesis and properties of (imidazo[1,2-a]benzimidazolyl-2)acetic acids
    Anisimova, V. A.
    Tolpygin, I. E.
    Spasov, A. A.
    Serdyuk, T. S.
    Sukhov, A. G.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2011, 37 (06) : 758 - 764
  • [50] STUDIES IN THE FIELD OF IMIDAZO[1,2-A]BENZIMIDAZOLE DERIVATIVES .22. SYNTHESIS OF 2,3-DIHYDROIMIDAZO[1,2-A]BENZIMIDAZOLES ON THE BASIS OF 2-IMINO-3-(2-HYDROXYETHYL)BENZIMIDAZOLINES
    ANISIMOVA, VA
    LEVCHENKO, MV
    POZHARSKII, AF
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (07): : 918 - 925
12345