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
  • [1] 4-(3-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)thieno[3,2-d]pyrimidine
    Noh, Eun Sun
    Kim, Sung Min
    Song, Yang-Heon
    MOLBANK, 2020, 2020 (02)
  • [2] Reaction of 7-phenyl-7H-pyrazolo-[3,4-d][1,2,3]triazin-4-ol with thionyl chloride
    Khutova, B. M.
    Klyuchko, S. V.
    Gurenko, A. O.
    Vasilenko, A. N.
    Rusanov, E. B.
    Brovarets, V. S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (06) : 922 - 929
  • [3] 4,5-Dihydro-1H-pyrazolo[3,4-d] pyrimidine containing phenothiazines as antitubercular agents
    Siddiqui, Arif B.
    Trivedi, Amit R.
    Kataria, Vipul B.
    Shah, Viresh H.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (06) : 1493 - 1495
  • [4] Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones
    Gautam, Poonam
    Chaudhary, R. P.
    HETEROCYCLIC COMMUNICATIONS, 2014, 20 (04) : 233 - 237
  • [5] Synthesis and Biological Activity of Some 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines/6-bromo-3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines
    Shukla, Davender Kumar
    Rani, Manju
    Khan, Arif Ali
    Tiwari, Kavita
    Gupta, Rajinder K.
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (11) : 5921 - 5924
  • [6] Synthesis of Pyrazolo[3,4-d]-4,5-dihydropyrimidines through [5+1] Cyclocondensation
    Ryabukhin, Sergey V.
    Granat, Dmitry S.
    Plaskon, Andrey S.
    Volochnyuk, Dmitriy M.
    Shivanyuk, Alexander N.
    SYNLETT, 2013, 24 (20) : 2675 - 2678
  • [7] Synthesis and Study of Antibacterial Effect of 3,4-Diaryl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
    Labhade, Kailas Rangnath
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL INVESTIGATION, 2022, 12 (02) : 173 - 177
  • [8] Regiocontrolled Synthesis of 6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazines
    Lindsay-Scott, Peter J.
    Rivlin-Derrick, Eloise
    SYNTHESIS-STUTTGART, 2020, 52 (01): : 105 - 118
  • [9] Design, synthesis of benzimidazole tethered 3,4-dihydro-2H-benzo[e] [1,3] oxazines as anticancer agents
    Gali, Srinivas
    Raghu, D.
    Mallikanti, Veerabhadraiah
    Thumma, Vishnu
    Vaddiraju, Namratha
    MOLECULAR DIVERSITY, 2024, 28 (03) : 1347 - 1361
  • [10] Synthesis of 2-Aryl-4-(R-sulfanylmethyl)-3-methyl-6,7-dihydro-2H-pyrazolo[3,4-d]pyridazin-7-ones
    Matiichuk, V. S.
    Potopnyk, M. A.
    Obushak, N. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (10) : 1550 - 1557