Synthesis of 6‐Cycloalkyl‐2(3H)‐benzoxazolones and Benzoxathiazolones via 6‐Tri‐N‐butyltin Intermediates

Abstract

Friedel–Crafts acylation of highly activated aromatic nuclei is rendered difficult by the fact that extensive complexation of the substrate by the Lewis acid catalyst inevitably takes place, which deactivates more or less completely such reagents. 2(3H)‐benzoxazolones and their sulfur bioisosters were chosen as model molecules in an effort to search for an efficient alternative method to the Friedel–Crafts reaction. 6‐Cycloalkylcarbonyl‐3‐methyl‐2(3H)‐benzoxazolones and benzothiazolones which cannot be synthesized by classical Friedel–Crafts approach are expeditiously obtained via tributyltin intermediates to afford the desired compounds in good yields.

Keywords:

• 2(3H)‐Benzoxazolone
• 2(3H)‐Benzothiazolone
• Organotin compounds