Anilides 9-acyl, indoles from

TV-Acyl indoles derived from amides have been employed for the conversion of lactones into protected hydroxyacids. Thus, (chloromethyl)alumi-num 2-(2-propenyl)anilide reacts (120) with 1,4- and 1,5-lactones, as for example per-O-terZ-butyldimethylsilyl-D-ribono-1,4-lactone (104), to afford hydroxyamides. After protection of the free hydroxyl group, these amides were converted by ozonolysis into TV-acyl indoles, 105, which were readily saponified to the acid 106. 

The aromatic amides have attracted considerable interest from the photochemical point of view. However, anilides are less prone to photochemical rearrangements than the analogous phenyl esters. For this reason, the side reactions involving other parts of the molecule may compete favorably with PFR. Shizuka started the study of anilides in the 1960, and thereafter a number of papers have appeared dealing with the PFR of A -acyl anilines, carbazoles, indoles, and so forth. 

Many of the known examples involve base-promoted carbanion formation from aromatic amides. For example, indol-2-one derivatives 161 have been made by treatment of N-acyl-o-haloanilines 160 with LDA in THF, or KNH2 in liquid ammonia [132-134] (Scheme 35). Similarly, a,P-unsaturated anilides 162 afford the ring-closed 3-alkylideneoxindoles 163 on irradiation and treat-... 

Acylation of Amines. Acylation of amines is also faster in the presence of DMAP, as is acylation of indoles, phosphorylation of amines or hydrazines, and conversion of carboxylic acids into anilides by means of Phenyl Isocyanate /3-Lactam formation from /3-amino acids has been carried out with DCC-DMAP, but epimerization occurs. ... 

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See also in sourсe #XX -- [ ]

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