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

Citation
Dl. Crabb et al., Preparation of [1,2,4]triazoloquinazolinium betaines and molecular rearrangements of putative [1,2,4]triazolo[4,3-a][1,3,5]triazinium betaines, J CHEM S P1, (11), 1999, pp. 1517-1525
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
11
Year of publication
1999
Pages
1517 - 1525
Database
ISI
SICI code
0300-922X(19990607):11<1517:PO[BAM>2.0.ZU;2-P
Abstract
3H-10 lambda(5)-[1,2,4]Triazolo[4,3-a]quinazolin-10-ylium-1-aminides were p repared by treating 1-methyl-1-(4-methylquinazolin-2-yl)-4-(aryl)thiosemica rbazides with dicyclohexylcarbodiimide (DCC); the crystal and molecular str ucture of one such derivative has been investigated by X-ray crystallograph y. A quinazolinium-1-olate and a-thiolate analogue of the aminides have als o been prepared. 2-(1-Methylhydrazino)-4,6-dimethyl-1,3,5-triazine was synt hesised by condensing the free base derived from 1-methyl-1-aminoguanidine sulfate with ethyl N-acetylacetamidate A series of thiosemicarbazides was p repared by treating the above hydrazine derivative with isothiocyanates. On e such thiosemicarbazide was treated with DCC to afford a 1,2,4,6-tetraazah exadiene derivative. Thermal reaction of 1-(4,6-dimethyl-1,3,5-triazin-2-yl )-1,3-dimethyl-4-(phenyl)isothiosemicarbazide gave a product of dimerisatio n, the structure of which was elucidated by X-ray crystallography.