Environmentally friendly Nafion-catalyzed synthesis of 3-substituted isoquinoline by using hexamethyldisilazane as a nitrogen source under microwave irradiation.

Abstract

This study developed an eco-friendly method to synthesize 3-arylisoquinoline from 2-alkynylbenzaldehydes using Nafion® NR50 as an acidic catalyst and hexamethyldisilazane (HMDS) as a nitrogen source. The reaction proceeded via a 6-exo-dig cyclization under microwave irradiation, giving the corresponding isoquinolines in excellent yields. The advantages of this protocol include: (1) the use of recyclable acid catalysts, (2) transition-metal-free catalysis, and (3) the effective formation of the target product. These features make this methodology a promising approach for the sustainable and efficient synthesis of 3-arylisoquinoline. Some structures were also confirmed by single-crystal X-ray diffraction analysis.