AlCl3-DMF Reagent in the Friedel-Crafts Reaction. Application to the Acylation Reaction of 2(3H)-Benzothiazolones

Development of New Insulin-like Growth Factor-1 Receptor Kinase Inhibitors Using Catechol Mimics

“…In addition to the higher yields and less drastic conditions, this has the advantage of yielding the isomeric benzoxazolone aldehydes 3 and 9. Friedel-Crafts acetylation of benzoxazolone yields only the 6-acetyl isomer (28). The bromoacetyl benzoxazolone 13 was prepared by this route.…”

Synthesis of 2(3H)‐benzoxazolone and 2(3H)‐benzothiazolone derivatives as potential beta‐3‐adrenergic receptor ligands (part 2)

“…Elemental analyses were performed by the "Service Central de Microanalyses", CNRS, Vernaison, France and are within ± 0.4% of the calculated values. Compounds 12 and 13 were synthesized according to the previously described procedures [9][10][11].…”

“…Starting from 6-(2-bromoacetyl)-3-methyl-2(3H)-benzoxazolone (12) [9,10] and its sulphured analogue 13 [11], a substitution reaction with the secondary amine 11 provide compounds 14 and 15 with 67% and 60% yield. Cleavage of the benzyl group by 1-chloroethyl chloroformate and methanol [12] afforded 16 and 17 with 70% and 75% yield, respectively.…”

The synthesis, antimicrobial activity studies, and molecular property predictions of novel benzothiazole-2-thione derivatives

“…Studies on the latter have shown that acylation of this ring system at the 6 th position can be achieved either by Friedel-Craft conditions or through the reaction of carboxylic and polyphosphoric acids 26 . Considering these findings, addition of a moderately electron withdrawing group such as benzoyl to the 6 th position of the benzothiazole-2-thione ring system and performing a Mannich reaction with the ring nitrogen can result in products with antimicrobial or antifungal activities.…”