Synthesis of some novel pyrazolo[1,5-a]pyrimidine, 1,2,4-triazolo[1,5-a]pyrimidine, pyrido[2,3-d]pyrimidine, pyrazolo[5,1-c]-1,2,4-triazine and 1,2,4-triazolo[5,1-c]-1,2,4-triazine derivatives incorporating a thiazolo[3,2-a]benzimidazole moiety

被引:35
|
作者
Abdel-Aziz, Hatem A. [1 ]
Hamdy, Nehal A. [1 ]
Farag, Ahmad M. [2 ]
Fakhr, Issa M. I. [1 ]
机构
[1] Natl Res Ctr, Appl Organ Chem Dept, Cairo 12622, Egypt
[2] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt
关键词
D O I
10.1002/jhet.5570450413
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
E-3-(N,N-Dimethylamino)-1-(3-methylthiazolo[3,2-a]benzimidazol-2-yl)prop-2-en-1-one (2) was synthesized by the reaction of 1-(3-methylthiazolo[3,2-a]benzimidazol-2-yl)ethanone (1) with dimethylformamide-dimethylacetal. The reaction of 2 with 5-amino-3-phenyl-1H-pyrazole (4a) or 3-amino-1,2,4-(1H)-triazole (4b) furnished pyrazolo[1,5-a]pyrimidine and 1,2,4-triazolo[1,5-a]pyrimidine derivatives 6a and 6b, while the reaction of enaminone 2 with 6-aminopyrimidine derivatives 7a,b afforded pyrido[2,3-d]pyrimidine derivatives 9a,b, respectively. The diazonium salts 11a or 11b coupled with compound 2 to yield the pyrazolo[5,1-c]-1,2,4-triazine and 1,2,4-triazolo[5,1-c]-1,2,4-triazine derivatives 13a and 13b. Some of the newly synthesized compounds exhibited a moderate effect against some bacterial and fungal species.
引用
收藏
页码:1033 / 1037
页数:5
相关论文
共 50 条
  • [21] A Facile Synthesis of Pyrido[2′,3′:3,4] pyrazolo[1,5-a] pyrimidine and Pyrido[2′,3′:3,4] pyrazolo[5,1-c][1,2,4] triazine Bearing a Thiophene Moiety
    Elsaman, Tilal
    Fares, Mohamed
    Abdel-Aziz, Hatem A.
    Attia, Mohamed I.
    Ghabbour, Hazem A.
    Dawood, Kamal M.
    JOURNAL OF CHEMISTRY, 2013, 2013
  • [22] ANTIMICROBIAL ACTIVITY OF NITRO-DERIVATIVES OF AZOLO[1,5-A]PYRIMIDINE AND AZOLO[5,1-C][1,2,4]TRIAZINE
    RUSINOV, VL
    MYASNIKOV, AV
    PILICHEVA, TL
    CHUPAKHIN, ON
    KIPRIANOVA, EA
    GARAGULYA, AD
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1990, 24 (01): : 39 - 40
  • [23] 1,2,4-TRIAZOLO[1,5]PYRIMIDINE DERIVATIVES ANNELATED BY CARBOCYCLES
    DESENKO, SM
    ESTRADA, H
    ORLOV, VD
    PONOMARYOV, OA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1991, (01): : 105 - 108
  • [24] 7-ethoxycarbonylmethyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine
    Fettouhi, M
    Boukhari, A
    ElOtmani, B
    Essassi, E
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1996, 52 : 1031 - 1032
  • [25] MECHANISM OF ACTION OF 1,2,4-TRIAZOLO[1,5-A]PYRIMIDINE SULFONAMIDE HERBICIDES
    SUBRAMANIAN, MV
    LONEY, V
    PAO, L
    PROSPECTS FOR AMINO ACID BIOSYNTHESIS INHIBITORS IN CROP PROTECTION AND PHARMACEUTICAL CHEMISTRY, 1989, 42 : 97 - 100
  • [26] Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo [1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles
    Al-Adiwish, Wedad M.
    Tahir, M. I. M.
    Siti-Noor-Adnalizawati, A.
    Hashim, Siti Farah
    Ibrahim, Nazlina
    Yaacob, W. A.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 64 : 464 - 476
  • [27] 1,2,4-Triazolo[5,1-b]- and -[1,5-a] quinazolines and their hydro derivatives
    Fischer, Gunther
    ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 135, 2021, 135 : 1 - 55
  • [28] Synthesis and properties of novel α-(1,2,4-triazolo[1,5-a] pyrimidine-2-oxyl) phosphonate derivatives
    Yang, GF
    Liu, ZM
    Liu, JC
    Yang, HZ
    HETEROATOM CHEMISTRY, 2000, 11 (04) : 313 - 316
  • [29] Ultrasound irradiation promotes the synthesis of new 1,2,4-triazolo [1,5-a]pyrimidine
    Frizzo, Clarissa P.
    Scapin, Elisandra
    Marzari, Mara R. B.
    Muenchen, Taiana S.
    Zanatta, Nilo
    Bonacorso, Helio G.
    Buriol, Lilian
    Martins, Marcos A. P.
    ULTRASONICS SONOCHEMISTRY, 2014, 21 (03) : 958 - 962
  • [30] Synthesis and antimicrobial activity of certain new 1,2,4-triazolo[1,5-a]pyrimidine derivatives
    Yaser A. -H. Mostafa
    Mostafa A. Hussein
    Awwad A. Radwan
    Abd El-Hamid N. Kfafy
    Archives of Pharmacal Research, 2008, 31