Back to Search
Start Over
Synthesis of Atropisomeric Benzoxazocines Based on Etherification Products of N-[2-(Cycloalk-1-en-1-yl)-phenyl]sulfonamides with Ethylene Chlorohydrin.
- Source :
-
Russian Journal of Organic Chemistry . Dec2023, Vol. 59 Issue 12, p2157-2166. 10p. - Publication Year :
- 2023
-
Abstract
- The reactions of N-[2-(cyclohex-1-en-1-yl)-6-methylphenyl]arenesulfonamides and N-[2-(cyclohex-1-en-1-yl)phenyl]methanesulfonamide with molecular bromine in the presence of ethylene chlorohydrin afforded mixtures of N-{2-[6-(2-chloroethoxy)cyclohex-1-en-1-yl]phenyl} sulfonamides and 9-(arenesulfonyl)- or 9-(methanesulfonyl)-2,3,9,9a-tetrahydro-1H-carbazoles. Intramolecular condensation of the obtained 2-chloro-ethyl ethers in the presence of potassium hydroxide and benzyl(triethyl)ammonium bromide in THF gave 8-(arenesulfonyl)-9-methyl-2,4,4a,6,7,8-hexahydro-3H-dibenzo[e,g][1,4]oxazocines as a result of forma-tion of new nitrogen–carbon bond. The presence of a methyl group at C9 of the aromatic ring gives rise to axial isomerism of the synthesized benzoxazocines. The major conformer of the cyclocondensation products has aS*,R* configuration of the heterocycle, and this conformer slowly isomerizes to the aR*,R* conformer at room temperature. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 10704280
- Volume :
- 59
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Russian Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 175456492
- Full Text :
- https://doi.org/10.1134/S1070428023120138