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.

Key words

one-pot reaction - sulfa-Michael addition - lactamization - pyrroloisoquinolone - sulfur-containing

• References


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Presumably due to the introduction of a Br atom at the ortho position of the aromatic ring (R²), atropisomeric product 3i was obtained with 2.5:1 diastereoselectivity. The structures of the isomers of 3i were confirmed by ¹H NMR and ¹³C NMR spectroscopy and by HRMS (see the experimental section). In the case of 3m, a single product was obtained and the phenomenon of restricted rotation was not observed. For atroposelective synthesis, please see:
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