876385-64-7Relevant academic research and scientific papers
Functiaonalization of 2-(1-Cyclohexen-1-yl)aniline Derivatives
Khusnitdinov,Sultanov,Gataullin
, p. 653 - 662 (2019/06/05)
The reaction of 2-(1-cyclohexen-1-yl)aniline and -6-methylaniline with phthalic anhydride has afforded 2-(2-cyclohex-1-en-1-ylphenyl)- and 2-(2-cyclohex-1-en-1-ylphenyl)-6-methylphenyl)-1H-isoindole-1,3(2H)-diones. The reaction of the obtained isoindole-1,3-diones with bromine in dichloromethane in the presence of sodium bicarbonate has led to the formation of the product of pseudo-allylic halogenation. Replacement of the halogen atom by methoxy group has been performed by keeping 2-[2-(6-bromocyclohex-1-en-1-ylphenyl)-6-methylphenyl)]-1H-isoindole-1,3(2H)-dione in a methanolic solution in the presence of NaHCO3. The reaction of 2-(2-cyclohex-1-en-1-yl-6-methylphenyl)-1H-isoindole-1,3(2H)-dione with molecular bromine in the presence of methanol has given a co-halogenation product, whereas the dibromination product has been obtained in the presence of octyl alcohol.
Reactions of N-and C-alkenylanilines: VII. Synthesis of indole heterocycles from products of reaction between N-mesyl-2-(1-alken-1-yl)anilines and halogens
Gataullin,Sotnikov,Spirikhin,Abdrakhmanov
, p. 715 - 722 (2007/10/03)
N-Mesyl-2-(1-methyl-1-butenyl)-6-methylaniline reacted with Br2 to afford N-mesyl-2-(3-bromo-1-penten-2-yl)aniline that under treatment with NH3 or amines underwent cyclization into N-mesyl-7-methyl-3- methylene-2-ethylindoline. The reaction of N-mesyl-2-(1-methyl-1-buten-1-yl)-4- methyl- and 2-(1-methyl-1-buten-1-yl)aniline with Br2 gave rise to the corresponding N-mesyl-2-(2-bromo-1-methyl-1-buten-1-yl)anilines. Under the similar conditions N-tosyl-2-(1-cyclohexen-1-yl)aniline was converted into N-tosyl-2-(6-bromo-1-cyclohexen-1-yl)aniline that under treatment with NH 3 furnished N-tosyl-1,2,3,9a-tetrahydrocarbazole. The reaction of N-mesyl-1,2,3,9a-tetrahydrocarbazole with CuBr2 in MeOH afforded N-mesyl-4-methoxy-1,2,3,4-tetrahydrocarbazole. N-Mesyl-6-methyl-2-(1- cyclopenten-1-yl)aniline in reaction with Br2 in the presence of NaHCO3 was oxidized into the corresponding cyclopentenone, and with NBS it gave N-mesyl-2-(2-bromo-1-cyclopenten-1-yl)aniline. 2005 Pleiades Publishing, Inc.
