Redox transformation of adducts from cycloaddition of diazoacetic ester to β-arylacryloyloxiranes

被引:0
|
作者
Mikhalenok S.G. [1 ]
Kuz'menok N.M. [1 ]
Zvonok A.M. [1 ]
机构
[1] Belarus State Technical University
关键词
β-arylacryloyloxiranes; 1,3-dipolar cycloaddition; 4,5-dihydro-1H-pyrazoles; Diazoacetic ester; Spectral characteristics;
D O I
10.1007/s10593-005-0264-7
中图分类号
学科分类号
摘要
It was established that, in addition to ethyl 4-aryl-3-(2,3-epoxyalkanoyl)- 4,5-dihydro-1H-pyrazole-5-carboxylates, the reaction of diazoacetic ester with β-arylacryloyloxiranes also gives ethyl 4-aryl-3(5)-(3-hydroxy-2- methylalkanoyl)-1H-pyrazole-5(3)-carboxylates. The latter are formed from the tautomeric ethyl 4-aryl-5-(2,3-epoxyalkanoyl)-4,5-dihydro-1H-pyrazole-3- carboxylates as a result of intramolecular oxidative-reductive disproportionation. © 2005 Springer Science+Business Media, Inc.
引用
收藏
页码:977 / 986
页数:9
相关论文
共 50 条
  • [31] Quench treatment cytochrome c: Transformation from a classical redox protein to a peroxidase like enzyme
    Niu, Nan-Nan
    Zhao, Wen-Jun
    Xiao, Bao-Lin
    Liang, Yu-Chen
    Meng, Xin
    Song, Xin-Yan
    Li, Di
    Hong, Jun
    Moosavi-Movahedi, Ali Akbar
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2022, 19 (06) : 2347 - 2357
  • [32] Selective [3+2] Huisgen Cycloaddition. Synthesis of Trans-Disubstituted Triazolodiazepines from Aza-Baylis-Hillman Adducts
    Declerck, Valerie
    Toupet, Loic
    Martinez, Jean
    Lamaty, Frederic
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05): : 2004 - 2007
  • [33] Possible implications of redox-sensitive tumour cell transformation; lessons from cell culture studies
    Orzechowski, A.
    POLISH JOURNAL OF VETERINARY SCIENCES, 2007, 10 (02): : 123 - 126
  • [34] Redox-induced transformation from an extended to a π-stacked conformer in acyclic bis(catecholacetal)s of acetylacetone
    Rathore, R
    Chebny, VJ
    Kopatz, EJ
    Guzei, IA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) : 2771 - 2774
  • [35] Synthesis of 3-nitro-1H-indole-2-carboxylic acid ethyl ester derivatives from Baylis-Hillman adducts
    Horn, CR
    Perez, M
    SYNLETT, 2005, (09) : 1480 - 1482
  • [36] Synthesis and stereochemistry of thiapyranothiazoles as Diels-Alder adducts obtained from spirodimers of 1,3-thiazolidines with cinnamic acid and its ester
    Omar, MT
    El-Khamry, A
    Youssef, AM
    Ramadan, S
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (04) : 721 - 735
  • [37] Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl - experimental and DFT computational study
    Kadina, Anastasia P.
    Khlebnikov, Alexander F.
    Novikov, Mikhail S.
    Perez, Pedro J.
    Yufit, Dmitry S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (29) : 5582 - 5591
  • [38] Ferrocenyl Quinone Methide-Thiol Adducts as New Antiproliferative Agents: Synthesis, Metabolic Formation from Ferrociphenols, and Oxidative Transformation
    Wang, Yong
    Richard, Marie-Aude
    Top, Siden
    Dansette, Patrick M.
    Pigeon, Pascal
    Vessieres, Anne
    Mansuy, Daniel
    Jaouen, Gerard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) : 10431 - 10434
  • [39] Synthesis of 2-benzylphenols: Transformation of the Baylis-Hillman adducts derived from 2-cyclohexen-1-one
    Lee, KY
    Na, JE
    Kim, JN
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (04) : 409 - 410
  • [40] CYCLOADDITION REACTIONS OF HETEROCUMULENES .21. [2-1]- AND [3-1]-ADDUCTS FROM ISOCYANATES AND 3-DIMETHYLAMINO-2H-AZIRINES
    SCHAUMANN, E
    GRABLEY, S
    ADIWIDJAJA, G
    LIEBIGS ANNALEN DER CHEMIE, 1981, (02): : 264 - 276