P methoxylation

The introduction of a p-methoxyl group on the phenacyl residue (82c, R = = H) allows a lower temperature, about 70°, for... 

Consider now, however, the solution-phase addition reaction84 of methanol to jD-nitrobenzalanilines substituted on the aniline ring cf. reaction 19. Nearly equal exother-micities of 11 1.3 and 10 13 kl ruol 1 are found for the parent and p -methoxylated species in this reaction that produces the correspondingly substituted (a-methoxy-4-nitrobenzyl)anilines. However, the experimental uncertainty of the latter reaction obscures any effect to be documented for the methoxy substituent. 

The transient absorptions of t-S decayed monotonously with first-order kinetics and did not show any shifts or spectral changes. The transient absorptions of c-2, and c-6 without p-methoxyl group (/)-MeO) decayed with kobs, in a similar way to those of t-1 8. On the other hand, formation of the band of t-3 -5 and t-8 " after e was observed with decay of the band of c-3 " -5" and c-8 " with p-MeO, respectively, k ... 

Likewise, Kishan and Sundaram (1985, 1980) report that substituted phenacyl bromides (CgHjCOBr) are oxidized (in 40-70% acetic acid/H2S04) without complex formation. The reaction is catalyzed by acid, but the pseudo-first-order fits depend on the initial [Ce(lV)]. This observation is attributed to the presence of an unreactive Ce(IV) trimer, which has been reported to be present in acetic acid solutions. The rate of reaction of phenacyl bromides substituted with either electron-withdrawing or electron-donating substituents is faster than that of unsubstituted phenacyl bromide. The activation parameters for the p-methyl and p-methoxyl substituents suggest that a different mechanism operates for these systems. Where comparable substituents exist, the rates for oxidation of phenacyl bromides compare favorably with those for benzaldehyde dted above. 

Langer and co-workers generated 2,2 -bis-quinazolin-4-ones by condensing substituted anthranilic esters with substituted bis(imidoyl)-chlorides. These compounds, which are structurally similar to the quinazoline alkaloid febrifUgine, have the potential to serve as anti-malarials. Treatment of methyl-2-amino-4,5-dimethoxybenzoate with bis(p-methoxyl-phenylimidoyl)chloride in the presence of two equivalents of TEA in refluxing toluene gave the desired product in 60% yield. 

Ho, J.-H. and Ho, T.-l. Novel photoreaction of N-alkyl(p-methoxyl)arylamines assisted by protic acids, /. Chem. Soc., Chem. Commun., 270-271, 2002. 

The composition of matter of claim 2 having the chemical name 2- o-methoxyphenyl)-4,5-bis(p-methoxyl) phenyl imidazolyl. 

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