Facile Synthesis of Multifunctional Pyrrolo[2,1-a]isoquinolin-3(2H)-ones via Sulfa-Michael-Triggered One-Pot Reactions

Abstract

An operationally simple and efficient one-pot method is developed for the synthesis of pyrrolo[2,1-a]isoquinolin-3(2H)-ones bearing sulfur moieties. The reaction involves a sulfa-Michael-triggered tandem reaction followed by acid-mediated lactamization, and exhibits good functional group tolerance.

Facile synthesis of pyrrolo[2,1-a]isoquinolines by domino reaction of 1-aroyl-3,4-dihydroisoquinolines with conjugated ketones, nitroalkenes and nitriles

“…The formation of the pyrrole ring proceeds in the presence of silver acetate, and this approach was also used in the synthesis of the alkaloid Crispine A [30]. Intramolecular reactions of 1-and 1,2-functionalized tetrahydro-, 1,2-and 3,4-dihydroisoquinolines are often used for annulation of the pyrrole core [31][32][33][34][35][36]. Recently, our group has demonstrated the preparation of functionally substituted on the pyrrole ring pyrrolo[2,1-a]isoquinolines based on domino reactions of 3,4-dihydro-1-aroylisoquinolines with electron-deficient alkynes, α,β-unsaturated aldehydes and cross-conjugated vinyl ethynyl ketones [37][38][39][40].…”