Redox isomerization via azomethine ylide intermediates: N-alkyl indoles from indolines and aldehydes.
Indolines react with aromatic and heteroaromatic aldehydes to yield N-alkyl indoles in a benzoic acid catalyzed redox isomerization reaction. Azomethine ylides are intermediates in this process which was established by intramolecular [3 + 2] trapping experiments.
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Indubhusan
I
Deb
Deepankar
D
Das
Daniel
D
Seidel
D000447:Aldehydes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D019817:Benzoic Acid / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
D000447:Aldehydes; D001391:Azo Compounds; D007211:Indoles; D013882:Thiosemicarbazones; C512188:azomethine; C057812:indoline; D019817:Benzoic Acid