Synthesis of novel naphtho[2,1-b]furopyrimidine derivatives

被引:0
|
作者
Mahadevan, KM [1 ]
Vaidya, VP [1 ]
Vagdevi, HM [1 ]
机构
[1] Kuvempu Univ, Dept Chem, Shankaraghatta 577451, Karnataka, India
关键词
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-Acyl-3-aminonaphtho[2,1-b]furans 2a-c are converted into corresponding oximes 3a-c,which on reaction with chloroacetyl chloride in the presence of triethyl. amine yield 2-chloromethyl-4-alkyl/arylnaphtho[2, 1-b]furo[3,2-d]pyrimidine-3-oxides 4a-c. Acylation of compounds 2a-c furnish 2-acyl-3-acylamidonaphtho[2,1-b]furans 5a-f, which undergo ring closure, on reacting with hydrazine hydrate and produce 2-alkyl/aryl-3,4-dihydro-3-amino-4-hydroxy-4-alkyl/aryl-naphtho[2,1-b]furo[3,2-d]pyrimidines 6a-f. Compounds 6a-f when refluxed with formic acid undergo ring opening and rearrangement simultaneously to give 2-acyl-3-(3'-alkyl/aryl-1',2',4'-triazol-4'-yl)naphtho[2,1-b]furans 7a-f. The compounds synthesized have been screened for antimicrobial, anthelmintic and anti-inflammatory activity.
引用
收藏
页码:1931 / 1936
页数:6
相关论文
共 50 条
  • [41] Novel synthesis of pyrido[2,1-b]benzothiazoles and 1,3-benzothiazole derivatives
    Elgemeie, GH
    Shams, HZ
    Elkholy, YM
    Abbas, NS
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 165 : 265 - 272
  • [42] Synthesis and antitumor evaluation of novel Benzo[d]pyrrolo[2,1-b]thiazole derivatives
    Chaniyara, Ravi
    Tala, Satishkumar
    Chen, Chi-Wei
    Lee, Pei-Chih
    Kakadiya, Rajesh
    Dong, Huajin
    Marvania, Bhavin
    Chen, Ching-Huang
    Chou, Ting-Chao
    Lee, Te-Chang
    Shah, Anamik
    Su, Tsann-Long
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 53 : 28 - 40
  • [43] Properties of naphtho[2,1-b]pyrans covalently linked to oligonucleotides
    Mazzei, M
    Sottofattori, E
    Ibrahim, M
    Balbi, A
    NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (9-11): : 1885 - 1894
  • [44] SYNTHESIS OF 2-AMINO-4-ARYL-4H-NAPHTHO[2,1-B]PYRANES
    SHARANIN, YA
    KLOKOL, GV
    ZHURNAL ORGANICHESKOI KHIMII, 1982, 18 (09): : 2005 - 2006
  • [45] Synthesis, antimicrobial and anthelminitic activities of 2,9-disubstituted naphtho [2,1-b] furans
    Chandrashekhar, C.
    Kumaraswamy, M. N.
    Basavaraja, K. M.
    Vaidya, V. P.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 16 (04) : 341 - 344
  • [46] Synthesis of naphtho[2,1-b]furanylium cation and its reaction with alcohols and trialkyl phosphites
    Yavari, I
    Anary-Abbasinejad, M
    Hossaini, Z
    POLISH JOURNAL OF CHEMISTRY, 2004, 78 (03) : 361 - 367
  • [47] 2-Methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan
    Choi, Hong Dae
    Seo, Pil Ja
    Son, Byeng Wha
    Lee, Uk
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O727 - U1532
  • [48] Combinatorial synthesis of imidazo[2,1-b]thiazole acyl derivatives
    Bunev, Alexander
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [49] 2-methyl-1-(methylsulfinyl)naphtho[2,1-b]furan
    Choi, Hong Dae
    Woo, Hyun Mi
    Seo, Pil Ja
    Son, Byeng Wha
    Lee, Uk
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O3881 - O3882
  • [50] Synthesis of 3-halogen derivatives of imidazo[2,1-b]- and benzimidazo[2,1-b][1,3]thiazines
    Kochergin, PM
    Bagry, AK
    Galenko, GF
    Kovpak, DV
    Aleksandrova, EV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (07): : 1004 - 1005