A one-pot, three-component regiospecific synthesis of dispiropyrrolidines containing a thiophenone ring via 1,3-dipolar cycloaddition reactions of azomethine ylides

摘要

The synthesis of new dispiropyrrolidines containing a thiophenone ring has been achieved by a one-pot, three-component 1,3-dipolar cycloaddition reaction. Unsaturated thiophenone dipolarophiles were reacted with azomethine ylides, generated in situ from sarcosine and cycloketone derivatives (isatin, nin-hydrin, acenaphthoquinone), to produce the corresponding cycloadducts in good yields (70-90%). The cycloaddition reaction was found to be highly regio- and diastereoselective.