TY - JOUR
T1 - Preparation of [1, 2, 4]triazoloquinazolinium betaines and molecular rearrangements of putative [1, 2, 4]triazolo[4, 3-a][1, 3, 5]triazinium betaines
AU - Crabb, Derek L.
AU - McCuliough, Kevin J.
AU - Preston, Peter N.
AU - Rosair, Georgina M.
AU - Bishop, Brian C.
AU - Wright, S. H B
AU - Clegg, William
AU - Coles, Simon
PY - 1999
Y1 - 1999
N2 - 3H-10?5-[1, 2, 4]Triazolo[4, 3-fl]quinazolin-10-ylium-l-aminides were prepared by treating 1-methyl-1-(4-methylquinazolin-2-yl)-4-(aryl)thiosemicarbazides with dicyclohexylcarbodiimide (DCC); the crystal and molecular structure of one such derivative has been investigated by X-ray crystallography. A quinazolinium-1-olate and a -thiolate analogue of the aminides have also been prepared. 2-(l-Methylhydrazino)-4, 6-dimethyl-l, 3, 5-triazine was synthesised by condensing the free base derived from 1-methyl-l-aminoguanidine sulfate with ethyl TV-acetylacetamidate. A series of thiosemicarbazides was prepared by treating the above hydrazine derivative with isothiocyanates. One-such thiosemicarbazide was treated with DCC to afford a 1, 2, 4, 6-tetraazahexadiene derivative. Thermal reaction of 1-(4, 6-dimethyl-1, 3, 5-triazin-2-yl)-1, 3-dimethyl-4-(phenyl)isothiosemicarbazide gave a product of dimerisation, the structure of which was elucidated by X-ray crystallography.
AB - 3H-10?5-[1, 2, 4]Triazolo[4, 3-fl]quinazolin-10-ylium-l-aminides were prepared by treating 1-methyl-1-(4-methylquinazolin-2-yl)-4-(aryl)thiosemicarbazides with dicyclohexylcarbodiimide (DCC); the crystal and molecular structure of one such derivative has been investigated by X-ray crystallography. A quinazolinium-1-olate and a -thiolate analogue of the aminides have also been prepared. 2-(l-Methylhydrazino)-4, 6-dimethyl-l, 3, 5-triazine was synthesised by condensing the free base derived from 1-methyl-l-aminoguanidine sulfate with ethyl TV-acetylacetamidate. A series of thiosemicarbazides was prepared by treating the above hydrazine derivative with isothiocyanates. One-such thiosemicarbazide was treated with DCC to afford a 1, 2, 4, 6-tetraazahexadiene derivative. Thermal reaction of 1-(4, 6-dimethyl-1, 3, 5-triazin-2-yl)-1, 3-dimethyl-4-(phenyl)isothiosemicarbazide gave a product of dimerisation, the structure of which was elucidated by X-ray crystallography.
UR - http://www.scopus.com/inward/record.url?scp=33746462231&partnerID=8YFLogxK
M3 - Article
SN - 0300-922X
SP - 1517
EP - 1525
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 11
ER -