The synthesis of new 2(3H )-benzoxazolinonylcarboxamides starting from 2-amino-4,6-dimethylpyridine and 2(3H )-benzoxazolone which were designed as anti-inflammatory agents is described. These derivatives were synthesised from 2(3H )-(benzoxazolinon-6-yl)carboxylic acids, which were obtained by Friedel-Crafts acylation of 2(3H )-benzoxazolone derivatives with oxalyl chloride and acetylchloride in the presence of the AlCl 3 -DMF complex. The constitution of the products was supported by elemental analysis IR and 1 H NMR spectral data.
With the aim to obtain 2(3H)-benzoxazolinones and 2(3H)-benzothiazolinone derivatives, we synthesized new imide compounds 5a-c, 6c-d and 7a-d by treating their 6-amino precursors with succinic, maleic or phthalic anhydride. The microwave (MW)-assisted reaction provided them more efficiently than through the corresponding isolated amic acids. The same nucleophile reagents were used in a MW-assisted formylation to obtain new formamide products 8-11, that were detected as cis/trans forms by NMR analysis. The ratio was in favor of the cis isomer and affected by the solvent, as also supported by DFT calculations.
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