A new conjugated addition of trialkyl phosphites and alkylidenephosphoranes to 3‐ω‐azideoacetyl coumarin synthesis of some 1,2,3,4‐triazaphospholes,triazoles, and azido‐coumarin derivatives

A new and efficient conjugate addition of trimethyl and triethyl phosphites to 3‐ω‐azidoacetylcoumarin ( 1 ) has been studied. The reaction proceeded smoothly at r.t. furnishing 1,2,3,4‐triazaphosphole coumarin derivatives 4a , 4b in ～75% yields. Linear substituted triazoles 10b , 11a were also obtained from the reactions of 1 with α‐keto ylides, acetyl‐ and benzoylmethylene triphenylphosphoranes. Contrary to these results, Wittig reaction was occurred when 1 was allowed to react with α‐alkoxycarbonylmethylene‐ and cyanomethylenetriphenylphosphoranes 7c , 7d , 7e as well as with methylidene‐ and benzylidenetriphenylphosphoranes 8b , 10a resulting in the formation of the corresponding olefins either as an intermediate 14b or as final products 11b , 11c , 12a . J. Heterocyclic Chem., (2011).