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

✍ Scribed by Brian L. Bray; Petr Hess; Joseph M. Muchowski; Markus E. Scheller

• Book ID: 102254399
• Publisher: John Wiley and Sons
• Year: 1988
• Tongue: German
• Weight: 244 KB
• Volume: 71
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19880710823

✦ Synopsis

The first known lithiated 1-azafulvene derivatives were generated by low-temperature halogen/metal interchange, with r-BuLi, from the corresponding brominated 6-diisopropylamino compounds 3b and 12. These Li species reacted with sundry electrophilic reagents to give products which, on basic hydrolysis, were converted into 5-mono-or 4,s-disubstituted pyrrole-2-carbaldehydes 10 and 16, respectively. ') *) 3, ' ) ' ) Contribution No. 735 from the Synrex Research, Institute of Organic Chemistry.