Synthesis of Epimethanetriyloxazoloand Epimethanetriylimidazobenzazocinones and -benzazoninones from syn- and anti-Atropisomers of N-Acyl-N-[2-(cycloalk-2-en-1-yl)-6-methylphenyl]glycines
- 作者: Aleksandrova L.A.1, Fatykhov A.A.1, Gataullina A.R.2, Kantor E.A.2, Gataullin R.R.1
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隶属关系:
- Ufa Institute of Chemistry
- Ufa State Petroleum Technological University
- 期: 卷 54, 编号 10 (2018)
- 页面: 1519-1530
- 栏目: Article
- URL: https://journals.rcsi.science/1070-4280/article/view/219252
- DOI: https://doi.org/10.1134/S1070428018100147
- ID: 219252
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详细
The major product of intramolecular [3 + 2]-cycloaddition of münchnones generated by heating syn- and anti-atropisomers of N-acetyl-N-[2-(cyclopent-2-en-1-yl)-6-methyl-, 2,4-dimethyl-, 2,5-dimethylphenyl)- and N-acetyl-N-[2-(cyclohex-2-en-1-yl)-6-methylphenyl]glycines with acetic anhydride was that formed from the anti isomer. Isomeric glycine derivatives having no methyl group in the ortho position of the aromatic ring gave rise to (1S*,3aR*,4S*,7S*,13S*)-1-methyl- and (1S*,3aR*,4S*,7S*,13S*)-3a-acetyl-1-methyl-4,5,6,7- tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin-3(3aH)-one as the major product. Treatment of 1,11-dimethyl- and 1,9,11-trimethyl-4,5,6,7-tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin- 3(3aH)-ones with methylamine in methanol on heating in a sealed ampule afforded epimethanetriylimidazobenzazocinones, whereas acid-stable compound with a methanocyclopenta[c]quinoline skeleton was formed under similar conditions from the 1,8,11-trimethyl analog.
作者简介
L. Aleksandrova
Ufa Institute of Chemistry
Email: gataullin@anrb.ru
俄罗斯联邦, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054
A. Fatykhov
Ufa Institute of Chemistry
Email: gataullin@anrb.ru
俄罗斯联邦, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054
A. Gataullina
Ufa State Petroleum Technological University
Email: gataullin@anrb.ru
俄罗斯联邦, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062
E. Kantor
Ufa State Petroleum Technological University
Email: gataullin@anrb.ru
俄罗斯联邦, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062
R. Gataullin
Ufa Institute of Chemistry
编辑信件的主要联系方式.
Email: gataullin@anrb.ru
俄罗斯联邦, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054
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