1011-24-1Relevant articles and documents
Mesoionic 1,2,4-triazolo[4,3-c]quinazolines
Gineinah,Ismaiel,El-Kerdawy,Glennon
, p. 723 - 726 (1990)
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Photoinduced molecular rearrangements. The photochemistry of some 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles. Formation of 1,2,4-triazoles, indazoles, and benzimidazoles
Buscemi, Silvestre,Vivona, Nicolo,Caronna, Tullio
, p. 8397 - 8401 (2007/10/03)
The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O-N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.
o.FORMYLARYLAZOMETHYLENETRIPHENYLPHOSPHORANES: A FACILE THERMALLY PROMOTED REARRANGEMENT TO 3-OXO-INDAZOLINE AND 4-OXO-DIHYDROQUINAZOLINE DERIVATIVES
Alemagna, A.,Buttero, P. del,Licandro, E.,Maiorana, S.,Papagni, A.
, p. 3321 - 3330 (2007/10/02)
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.