SURPRISING REACTIONS OF SPECIAL AZOOLEFINS - SELF-ARYLATION, INDOLE RING CLOSURE, MILD CHLORINE SUBSTITUTION, AND "TERT. AMINO EFFECT"

Article abstract of DOI:10.1016/S0040-4039(00)94252-7

Azoolefins 2 either decompose or react with aryldiimines with uptake of an aryl group to give compounds 3.The latter can undergo ring closure to N-amino-indoles 4.In the 2,4,6-trichloro compound 3b orthochlorines are selectively replaced by morpholine under very mild conditions giving 5a, which easily fragments to form the benzimidazole 7.