- 1H-1,3-diazepines and ketenimines from cyanotetrazolopyridines
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Cyano-substituted tetrazolo[1,5-a]pyridines/2-azidopyridines 8T and 15T undergo thermal ring opening to the azides 8A and 15A. Solution photolysis causes nitrogen elimination and ring expansion to 1,3-diazacyclohepta-1,2,4,6- tetraenes 10 and 17, which react with alcohols to afford 2-alkoxy-1H-1,3- diazepines, with secondary amines to 2-dialkylamino-5H-1,3-diazepines, and with water to 1,3-diazepin-2-ones (1214, 19, 21). Argon matrix photolysis of the azides affords the diazacycloheptatetraenes 10 and 17 as principal products together with ring-opened dicyanovinylketenimines 11 and 18. The matrix-isolated species were identified on the basis of comparison of the infrared spectra with those calculated at the B3LYP/631+G*level. CSIRO 2008.
- Addicott, Chris,Wentrup, Curt
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- Conversion of pyridine N -oxides to tetrazolopyridines
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An efficient and convenient procedure for the conversion of pyridine N-oxides to tetrazolopyridines by treatment with 4-toluene sulfonyl chloride and sodium azide in toluene at elevated temperature is described.
- Liu, Shanshan,Lentz, Dieter,Tzschucke, C. Christoph
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p. 3249 - 3254
(2014/05/06)
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