Edward L. Engelhardt

N-trimethylsilylpyrroles as dienes in the synthesis of 1,4-dihydronaphthalen-1,4-imines and isoindoles†

A convenient, general synthetic method for 1,4-dihydronaphthaIen-1,4-imines via the Diels-Alder addition of benzyne to N-trimethylsilylpyrrole is described. The N-trimethylsilyl protecting group protected the product from secondary benzyne reactions and was easily removed. The use of a 1,3-dipolar reagent to convert 1,4-dihydronaphthalen-1,4-imines to isoindoles via a retro-Diels-Alder sequence is illustrated.

Nucleophilic displacement of activated aryl triflates a new synthesis of oxindoles and arylacetic acids

Abstract 2-Nitroaryl triflates undergo efficient base-catalyzed nucleophilic displacement by dimethyl malonate anion to yield dimethyl nitroarylmalonates, which subsequently are converted in high yields to nitroarylacetic acids and oxindoles.