21250-36-2Relevant academic research and scientific papers
Aluminium chloride-catalyzed intermolecular vs intramolecular friedel-crafts reaction of acrylanilides and 3-chloropropanamides
Chen, I.-Li,Wang, Tai-Chi,Chen, Yeh-Long,Tzeng, Cherng-Chyi
, p. 155 - 162 (2007/10/03)
3-Phenylpropionanilide (4a) is obtained in a yield of 89% from acrylanilide by the treatment with AlCl3/ benzene, compared with a yield of 39% by the 1,4-conjugate addition of phenyllithium. The formation of 4a indicated that an intermolecular Friedel-Crafts reaction occurred, rather than the relatively more facile intramolecular ring cyclization, and provided a more efficient route than a conjugate addition of phenyllithium for the preparation of 3-phenylpropionanilide and its derivatives. Although the methoxy group is an activator of the nucleophilic substitution, introduction of a methoxy substituent at N-phenyl did not increase the competitive capability of the intramolecular cyclization because of AlCl3-catalyzed demethylation to form the ArOAlCl2 complex which decreased the availability of the π-electron in the N-phenyl aromatic system.
FOTOQUIMICA DE -TOLUIDIDAS DE ACIDOS αβ-INSATURADOS. INFLUENCIA DE LA ADICION DE CARBONATO POTASICO
Barbera, Carmen,Garcia, Hermenegildo,Miranda, Miguel Angel,Primo, Jaime
, p. 95 - 102 (2007/10/02)
Irradiation of the p-toluidides of crotonic and cinnamic acids (2a,c) gives rise predominantly to the cis isomers 5a,c, together with appreciable amounts of 4,6-dimethyl-3,4-dihydro-2-quinolone (6a) in the case of 2a.The corresponding photo-Fries products have not been detected, even when the irradiation is performed in the presence of K2CO3.By contrast, photolysis of the p-toluidides of methylcrotonic and phenylpropiolic acids (2b,d) gives rise to the o-aminophenones 7b,d (in addition to the quinolone 6b from 2b).For these two amides, as well as for acetanilide and benzanilide, the selectivity towards the acyl migration product markedly increases when the irradiation is performed in the presence of K2CO3.Key words: Enamides' photocyclization, photo-Fries, quinolones.
