The reactions of N-substituted 2-(dimethylallyl)aniline compounds with phenylselanyl halides

Citation
Ma. Cooper et al., The reactions of N-substituted 2-(dimethylallyl)aniline compounds with phenylselanyl halides, AUST J CHEM, 53(2), 2000, pp. 123-129
Citations number
27
Categorie Soggetti
Chemistry
Journal title
AUSTRALIAN JOURNAL OF CHEMISTRY
ISSN journal
00049425 → ACNP
Volume
53
Issue
2
Year of publication
2000
Pages
123 - 129
Database
ISI
SICI code
0004-9425(2000)53:2<123:TRON2C>2.0.ZU;2-Y
Abstract
Cyclization of the carbamate of 2-(dimethylallyl)aniline with phenylselanyl chloride (benzeneselenenyl chloride) gave a 1:1 mixture of a dihydroindole and a tetrahydroquinoline. With phenylselanyl bromide only the dihydroindo le was obtained. Addition of methanol to the silica used in the procedure t rapped the reaction at the non-cyclized stage forming a 3-methoxy-3-methyl- 2-(phenylselanyl)butyl side chain. The sulfonamide of 2-(dimethylallyl)anil ine only formed the dihydroindole with phenylselanyl chloride. The correspo nding trifluoroacetamide derivative did not form any cyclized product under the same conditions. The dihydroindole could be converted into the corresp onding alkene by oxidative removal of the phenylseleno group. 4-Ethoxycarbo nyl-2-(3,3-dimethylallyl)aniline cyclized with mercuric nitrate to give, af ter a reductive workup, a 2,2-dimethyltetrahydroquinoline. The X-ray crysta l structures of ethyl N-{2-[3-methoxy-3-methyl-2-(phenylselanyl)butyl] phen yl} carbamate and 2-[1-methyl-1-(phenylselanyl)ethyl]-1-[(4-methylphenyl)su lfonyl]indoline are reported.