95309-30-1Relevant articles and documents
Rearrangement Reactions of 1,3,6-Triaryl-1,4-dihydro-s-tetrazines leading to 2,4-Diarylquinazolines, 1-Anilino-3,5-diaryl-1H-1,2,4-triazoles, 1,3,5-Triaryl-1H-1,2,4-triazoles, and 2,5-Diaryl-1H-1,3,4-oxadiazoles. X-ray Structure Determination of 6-Isopropyl-2,4-diphenylquinazoline
Hunter, Daniel,Neilson, Douglas G.,Weakley, Timothy J.R.
, p. 2709 - 2712 (2007/10/02)
1,3,6-Triaryl-1,4-dihydro-s-tetrazines (2c-g) rearrange on heating at ca. 200 deg C to 2,4-diarylquinazolines (for which an X-ray determination was carried out on the 6-isopropyl compound) and 1-anilino-3,5-diaryl-1H-1,2,4-triazoles as major products.Hydrolysis in chloroform solution of the title compounds (2) and their 1-alkyl analogues gives rise to 1-aryl (or alkyl)-3,5-diaryl-1H-1,2,4-triazoles and 2,5-diaryl-1,3,4-oxadiazoles.
Thermal Rearrrangement of 1-Alkyl-3,6-diaryl-1,4-dihydro-s-tetrazines to 1-Alkylamino-3,5-diaryl-1,2,4-triazoles
Hunter, Daniel,Neilson, Douglas G.
, p. 2779 - 2783 (2007/10/02)
s-Tetrazines having aryl substituents in either the 3- or 3,6-positions react readily with alkyl or aryl Grignard reagents to give 1-alkyl(or aryl)-1,4-dihydro-s-terazines.The 1-alkyl-1,4-dihydro-s-tetrazines rearrange in methanolic hydrogen chloride to 4-alkylamino-1,2,4-triazoles, but thermolyse readily to the less well known, isomeric 1-alkylamino-1,2,4-triazoles.Possible reaction pathways involving breakdown to nitrile and reactive intermediates such as 1,3-dipolar species are discussed.