216. Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6-(Diisopropylamino)-1-azafulvene Derivatives. Novel Synthesis of 5-Mono- and 4,5-Disubstituted 1H-Pyrrole-2-carbaldehydes

Article abstract of DOI:10.1002/hlca.19880710823

The first known lithiated 1-azafulvene derivatives were generated by low-temperature halogen/metal interchange, with t-BuLi, from the corresponding brominated 6-diisopropylamino compounds 3b and 12.These Li species reacted with sundry electrophilic reagents to give products which, on the basic hydrolysis, were converted into 5-mono- or 4,5-disubstituted pyrrole-2-carbaldehydes 10 and 16, respectively.