Reaction Products of Activated Aromatic and Heteroaromatic Chlorides with N,N-Disubstituted Formamides

Abstract

Several N,N-disubstituted aromatic amines (3a–g) was obtained in very good yield by the reaction of adequate doubly activated aromatic or heteroaromatic halides (1a–e) with N,N-disubstituted formamides (2a–c). Analogously, starting from 4-chloro-3-pyridinesulfonamide, the appropriate 4-dialkylamino-1H ⁺-pyridinium-3-(N-formyl)sulfonamidates (5a,b) were obtained in 52–60% yield. Mechanisms of the reactions are discussed.

Keywords:

• Activated aromatic chlorides
• amination and formylation reaction products
• N,N-disubstituted formamides