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Preparation of [1, 2, 4]triazoloquinazolinium betaines and molecular rearrangements of putative [1, 2, 4]triazolo[4, 3-a][1, 3, 5]triazinium betaines

Lookup NU author(s): Professor William Clegg

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Abstract

3H-10λ5-[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.

Publication metadata

Author(s): Crabb DL, McCuliough KJ, Preston PN, Rosair GM, Bishop BC, Wright SHB, Clegg W, Coles S

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society - Perkin Transactions 1

Year: 1999

Issue: 11

Pages: 1517-1525

Print publication date: 01/01/1999

ISSN (print): 0300-922X

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/a900941h

DOI: 10.1039/a900941h

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