Tetrahedron p. 3321 - 3330 (1985)
Update date:2022-08-04
Topics:
Alemagna, A.
Buttero, P. del
Licandro, E.
Maiorana, S.
Papagni, A.
The o.formylarylazomethylenetriphenylphosphoranes carrying an electron withdrawing group on the ylidic carbon undergo thermal intramolecular cyclization to 3-oxo-indazolin-2-yl-methylenephosphorane derivatives.The latter compounds, and their 1-alkyl derivatives, in turn, undergo thermal and/or acid catalyzed rearrangement to 4-oxo-1,4-dihydroquinazoline derivatives and PPh3.Some possible reaction mechanisms are discussed, and some synthetic applications of the above reactions are shown.
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