54903-06-9Relevant articles and documents
Radical cyclisation reactions with indoles
Flanagan, Stuart R.,Harrowven, David C.,Bradley, Mark
, p. 1795 - 1798 (2003)
Several radical cyclisation reactions involving indoles are described. Most notably, we have shown that radical additions to C3 of an indole are frequently facile. A dichotomy in the course of radical cyclisation reactions to C2 of the indole has also been exposed wherein 6-endo-trig cyclisations are propagated by the loss of a hydrogen atom from C2 while 5-exo-trig cyclisations are propagated by hydrogen atom abstraction at C3 from tributyltin hydride. Cyclisations involving the addition of indolyl radical intermediates to arenes have also been demonstrated.
Light-induced Reactions of 2-(N-Alkyl-N-arylamino)acetophenones and Related Amino-ketones: Formation of 1,3-Diarylazetidin-3-ols
Allworth, Keith L.,EI-Hamamy, Ahmad A.,Hesabi, Massoud M.,Hill, John
, p. 1671 - 1678 (2007/10/02)
On irradiation in ether, 2-(N-methylanilino)acetophenones, Ar1NMe-CH2COAr2 (Ar1,Ar2=Ph,Ph; Ph,p-MeO-C6H4; Ph,p-Ph-C6H4; p-Cl-C6H4,Ph; p-MeO-C6H4,Ph; and p-Me-C6H4,Ph), underwent type II cyclisation to isomeric 1,3-diarylazetidin-3-ols.A minor photoproduct was one of the two expected type II fission products, the corresponding acetophenone Ar2COMe.The second type II fission product, imine Ar1N=CH2, was not detected, but in three cases a 1,3-diarylimidazolidine, probably derived from this imine, was isolated.Similar results were obtained on irradiation of the related amino-ketones, 2-(N-methylanilino)-2'-acetonaphthone and 2-(N-methylanilino)-1-tetralone.Direct fission of the C-2-N bond occured on irradiation of 2-(N-methylanilino)indan-1-one and 2,2-dimethyl-2-(N-methylanilino)acetophenone. 2-(N-Alkylanilino)acetophenones, PhNR-CH2COPh (R=Et, Me2CH, and PHCH2), yielded complex mixtures on irradiation.
