Details

Autor(en) / Beteiligte

• Aleksandrova, L. A.
• Fatykhov, A. A.
• Gataullina, A. R.
• Kantor, E. A.
• Gataullin, R. R.

Titel

Synthesis of Epimethanetriyloxazoloand Epimethanetriylimidazobenzazocinones and -benzazoninones from syn- and anti-Atropisomers of N-Acyl-N-[2-(cycloalk-2-en-1-yl)-6-methylphenyl]glycines

Ist Teil von

• Russian journal of organic chemistry, 2018-10, Vol.54 (10), p.1519-1530

Ort / Verlag

Moscow: Pleiades Publishing

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 (1 S *,3a R *,4 S *,7 S *,13 S *)-1-methyl- and (1 S *,3a R *,4 S *,7 S *,13 S *)-3a-acetyl-1-methyl-4,5,6,7- tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4- a ][1]benzazocin-3(3a H )-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(3a H )-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.