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

Derek L. Crabb, Kevin J. McCuliough, Peter N. Preston, Georgina M. Rosair, Brian C. Bishop, S. H B Wright, William Clegg, Simon Coles

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)1517-1525
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number11
Publication statusPublished - 1999

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Betaine
Dicyclohexylcarbodiimide
hydrazine
X ray crystallography
Derivatives
Isothiocyanates
Triazines
Dimerization
Molecular structure
Crystal structure
thiosemicarbazide

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Crabb, D. L., McCuliough, K. J., Preston, P. N., Rosair, G. M., Bishop, B. C., Wright, S. H. B., ... Coles, S. (1999). Preparation of [1, 2, 4]triazoloquinazolinium betaines and molecular rearrangements of putative [1, 2, 4]triazolo[4, 3-a][1, 3, 5]triazinium betaines. Journal of the Chemical Society, Perkin Transactions 1, (11), 1517-1525.
Crabb, Derek L. ; McCuliough, Kevin J. ; Preston, Peter N. ; Rosair, Georgina M. ; Bishop, Brian C. ; Wright, S. H B ; Clegg, William ; Coles, Simon. / Preparation of [1, 2, 4]triazoloquinazolinium betaines and molecular rearrangements of putative [1, 2, 4]triazolo[4, 3-a][1, 3, 5]triazinium betaines. In: Journal of the Chemical Society, Perkin Transactions 1. 1999 ; No. 11. pp. 1517-1525.
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abstract = "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.",
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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. / Crabb, Derek L.; McCuliough, Kevin J.; Preston, Peter N.; Rosair, Georgina M.; Bishop, Brian C.; Wright, S. H B; Clegg, William; Coles, Simon.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 11, 1999, p. 1517-1525.

Research output: Contribution to journalArticle

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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

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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.

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