A Brønsted acid-catalyzed thioacid addition to in situ -generated aldimine for the synthesis of isoindolinones with the N , S -acetal framework.

A facile methodology was demonstrated for the synthesis of isoindolinones containing the N , S -acetal framework by employing a Brønsted acid catalyst with a three-component reaction. The reaction proceeded via the addition of thioacid to in situ -generated aldimine followed by lactamization, which involved the formation of one C-S bond and two C-N bonds under easily controlled and ambient reaction conditions. A variety of substituted isoindolinones were synthesized with up to 99% yields. Furthermore, the importance of this methodology was also justified by a gram-scale synthesis and demonstration of some interesting synthetic transformations.