N-trimethylsilylpyrroles as dienes in the synthesis of 1,4-dihydronaphthalen-1,4-imines and isoindoles |
| |
| Authors: | P S Anderson M E Christy E L Engelhardt G F Lundell C S Ponticello |
| |
| Abstract: | 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. |
| |
| Keywords: | |
|
|
