An Efficient Synthesis of 7-(Arylmethyl)-3-tert-butyl-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazines

被引:25
|
作者
Abonia, Rodrigo [1 ]
Castillo, Juan [1 ]
Insuasty, Braulio [1 ]
Quiroga, Jairo [1 ]
Nogueras, Manuel [2 ]
Cobo, Justo [2 ]
机构
[1] Univ Valle, Dept Quim, Cali 25360, Colombia
[2] Univ Jaen, Dept Quim Inorgan & Organ, Jaen 23071, Spain
关键词
5-Aminopyrazoles; Etherification; Pyrazolo-oxazines; Heterocycles; Cyclization; Fused-ring systems; DERIVATIVES;
D O I
10.1002/ejoc.201000678
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and three-step procedure for the synthesis of novel 6,7-dihydro-1H,4H-pyrazolo[3,4 -d][1,3]oxazine derivatives in good to excellent yields by treatment of pyrazol-amines with aqueous formaldehyde in the presence of acetic acid is provided. The reactions proceeded through an intramolecular etherification process by dehydration of a 1,5-diol intermediate formed in the course of the reaction and promoted by acid media.
引用
收藏
页码:6454 / 6463
页数:10
相关论文
共 50 条
  • [21] Theoretical and experimental investigations on the structure and vibrational spectra of 6-amino-3-methyl-1-phenyl-1H-pyrazolo-[3,4-b]pyridine-5-carboxylic acid and 6,7-dihydro-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
    Bahgat, Khaled
    Jasem, Nazm Al-Den
    El-Emary, Talaat
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2009, 74 (05) : 555 - 571
  • [22] Theoretical explorations on the molecular structure and IR frequencies of 3-phenyl-1-tosyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine in view of experimental results
    Shukla, Bindesh Kumar
    Yadava, Umesh
    Roychoudhury, Mihir
    JOURNAL OF MOLECULAR LIQUIDS, 2015, 212 : 325 - 330
  • [23] Chemoselective Synthesis of Structurally Diverse 3,4-Dihydroquinazoline-2(1H)-thiones and 4H-Benzo[d][1,3]thiazines
    Dong, Jian-Lian
    Wei, Pei-Shun
    Yu, Li-Si-Han
    Xie, Jian-Wu
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) : 2219 - 2226
  • [24] An efficient Synthesis and Photophysical Properties of 1H-pyrazolo-[3,4-b]pyridine and pyrazolo[3,4-b][1,8]naphthyridines
    Deore, Raviraj
    Dingore, Kunal
    Jachak, Madhukar
    JOURNAL OF FLUORESCENCE, 2015, 25 (06) : 1549 - 1557
  • [25] Spectral emission properties of 4-aryloxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]quinolines
    Pokladko, M.
    Gondek, E.
    Sanetra, J.
    Niziol, J.
    Danel, A.
    Kityk, I. V.
    Reshak, Ali H.
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2009, 73 (02) : 281 - 285
  • [26] Synthesis and in vitro anticancer activity of pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-d][1,2,3]triazines
    Hassan, Ashraf S.
    Moustafa, Gaber O.
    Awad, Hanem M.
    SYNTHETIC COMMUNICATIONS, 2017, 47 (21) : 1963 - 1972
  • [27] Conversions of 7-aryl-7H-pyrazolo[3,4-d]-[1,2,3]triazin-4-ols by the action of phosphorus pentoxide, pentasulfide, and oxychloride
    Khutova, B. M.
    Klyuchko, S. V.
    Gurenko, A. O.
    Vasilenko, A. N.
    Balya, A. G.
    Rusanov, E. B.
    Brovarets, V. S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (08) : 1251 - 1262
  • [28] Reaction of 6-hydrazino-3,4-dimethyl-1H-pyrazolo[3,4-d]pyrimidine with pregnenolone derivatives
    A. V. Komkov
    I. V. Zavarzin
    A. S. Shashkov
    Russian Chemical Bulletin, 2014, 63 : 462 - 468
  • [29] Reaction of 6-hydrazino-3,4-dimethyl-1H-pyrazolo[3,4-d]pyrimidine with pregnenolone derivatives
    Komkov, A. V.
    Zavarzin, I. V.
    Shashkov, A. S.
    RUSSIAN CHEMICAL BULLETIN, 2014, 63 (02) : 462 - 468
  • [30] Synthesis of glycosides of 1H-Pyrazolo[3,4-b]pyridin-3(2H)-ones
    Supe, Linda
    Hein, Martin
    Iaroshenko, Viktor O.
    Villinger, Alexander
    Langer, Peter
    TETRAHEDRON, 2020, 76 (44)