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
  • [31] 5-(Pyridin-4-ylmethyl)-1H-pyrazolo-[ 3,4-d]pyrimidin-4(5H)-one
    Alsubari, Abdulsalam
    Ramli, Youssef
    Essassi, El Mokhtar
    Zouihri, Hafid
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1926 - U2015
  • [32] Synthesis, Crystal Structure and Biological Activities of Phenyl(6-phenyl-3-p-tolyl-6,7-dihydro-5H-[1,2,4]triazolo-[3,4-b] [1,3,4] thiadiazin-7-yl)methanone
    Ding Qi-Chun
    Zou Yi-Hui
    Li Qiu-Ling
    Huang Jian-Jun
    Zhang Li-Xue
    Yin Hui-Yong
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39 (08) : 1531 - 1538
  • [33] Regioselectivity of 1,3-dipolar cycloadditions and antimicrobial activity of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-diones, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines
    Zaki, Yasser Hassan
    Sayed, Abdelwahed Rashad
    Elroby, Shaaban A.
    CHEMISTRY CENTRAL JOURNAL, 2016, 10
  • [34] Palladium mediated regioselective intramolecular Heck reaction: synthesis of 1,3,4-trisubstituted pyrazolo[3,4-b]pyridines, 3H-pyrazolo[3,4-c]-isoquinolines and 3H-pyrazolo[4,3-f][1,7]-naphthyridines
    Prakash, Rashmi
    Shekarrao, Kommuri
    Saikia, Pallabi
    Gogoi, Sanjib
    Boruah, Romesh C.
    RSC ADVANCES, 2015, 5 (27): : 21099 - 21102
  • [35] Crystal structure determination and analyses of Hirshfeld surface, crystal voids, intermolecular interaction energies and energy frameworks of 1-benzyl-4-(methylsulfanyl)-3a,7a-dihydro-1H-pyrazolo[3,4-d]pyrimidine
    Mustaphi, Nour El Hoda
    Chlouchi, Amina
    El Hafi, Mohamed
    Mague, Joel T.
    Hokelek, Tuncer
    El Monfalouti, Hanae
    Haoudi, Amal
    Mazzah, Ahmed
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2024, 80 : 783 - +
  • [36] Synthesis, characterisation and antimicrobial activity of 3-methyl-6-(aryl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine
    Girisha, K. S.
    Kalluraya, Balakrishna
    Jois, Vidyashree H. S.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (12): : 1767 - 1770
  • [37] Synthesis of Some 1,3-Dimethyl-6-substituted-1H-pyrazolo[3,4-b]pyrazin-5(4H)-ones
    Abu Safieh, Kayed A.
    Al-Masri, Feda'a S.
    Ayoub, Mikdad T.
    El-Abadelah, Mustafa M.
    Voelter, Wolfgang
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2011, 66 (11): : 1136 - 1140
  • [38] Recent methods for the synthesis of fused pyrazolo[3,4(4,3)-d]thiazoles and pyrazolo[3,4(4,3)-d][1,4]thiazines (microreview)
    Khodykina, Evgeniya S.
    Kolodina, Alexandra A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (9-10) : 634 - 636
  • [39] One pot multicomponent synthesis of 3′,5-diaryl-1′-phenyl-3,4-dihydro-1′H,2H-3,4′-bipyrazoles and their antimicrobial activity
    Ashok, D.
    Ganesh, Arram
    Ravi, S.
    Lakshmi, B. Vijaya
    Ramesh, B.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (11) : 2248 - 2256
  • [40] The synthesis of 3-(het)aryl-6,7-dihydro-5H-[1,2,4]-triazolo[3,4-a][2]benzazepines
    Glushkov, Vladimir A.
    Babentsev, Dmitry N.
    Dmitriev, Maksim V.
    Stepanova, Kseniya A.
    Kharintseva, Anastasiya Yu.
    Simakhina, Anastasiya E.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (01) : 63 - 68