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TworoutesarereportedforthesynthesisofiminocyclobutenoneshavingN-(het)arylsubstitution:anaddition/substitution sequence starting with cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein’s reagent and subsequent deprotonationundernon-hydrolyticconditions. Lithiumorganylswere foundtoaddtothe remainingcarbonylgroup. The resultingtertiaryalcoholsundergoringenlargementonheatinginxylenetogive4-aminophenols,4-amino-1-naphthols,or cyclopenta-annulated quinolines from 4-vinyl, 4-aryl, and 4-alkynyl derivatives, respectively.

New Syntheses and Ring Expansion Reactions of Cyclobutenimines