Formylation and Acylation of Organic Compounds With Substituted Amides of Carboxylic Acids

Naphthaldehydes

“…Naphthalene does not react with the milder formylating Vilsmeier reagent 19,20 (a mixture of POCl 3 with N,N-dimethylformamide or other formamide derivatives, for example, with N-methylformanilide). However, the reaction of acenaphthene performed under these conditions afforded acenaphthene-5-carbaldehyde (8) (81% yield).…”

“…35 The reaction of a-naphthol with a,a-dichlorodimethyl ether in the presence of TiCl 4 (Rieche method) afforded a mixture of aldehydes 17 and 18 in 68% and 10% yields, respectively. 35 Formylation of b-naphthol (19) gave rise to 2-hydroxy-1naphthaldehyde (20) regardless of the method used. The Gattermann reaction with the use of the HCN ± ZnCl 2 system 33 or the Zn(CN) 2 ± HCl system 14 produced aldehyde 20 in virtually quantitative yield.…”

“…40 3-Hydroxy-2-naphthoic acid is subjected to Vilsmeier formylation at position 4. 19 Formylation of alkoxynaphthalenes proceeds much as that of naphthols, although there are some exceptions. For example, Gattermann 43 or Vilsmeier 44 formylation of 1-methoxynaphthalene gave 4-methoxy-1-naphthaldehyde (28) in nearly quantitative yield (the reaction with the use of triformamide as the formylating agent, aldehyde 28 was prepared in only 42% yield).…”

The Vilsmeier–Haack formylation of 2,3-dihydro-4H-1,3-benzoxazin-4-ones and isomeric 1,2-dihydro-4H-3,1-benzoxazin-4-ones: an effective approach to functionalized 2H-/4H-chromenes and tetrahydroacridines

“…The Vilsmeier-Haack reaction is a powerful tool in modern synthesis and is widely used not only to introduce the CHO group into activated aromatic and heteroaromatic substrates, but also as an approach for various condensations and cyclizations (for reviews on the Vilsmeier-Haack reaction see [1][2][3][4][5][6].…”

Vilsmeier−Haack Reaction of 1-Cyclopropyl-2-arylethanones

“…Among the versatile useful applications, the carbon−carbon bond-forming reactions of the Vilsmeier reagent with aliphatic substrates, particularly carbonyl compounds containing a methyl or methylene group adjacent to the carbonyl group, have been the interest of many organic chemists. Though the Vilsmeier−Hacck reaction is widely used and will continue to be an active and fruitful research area, there is a significant limitation because the weakly electrophilic Vilsmeier reagent reacts efficiently only with electron-rich aromatic systems. , …”