Article abstract of DOI:10.1080/10426509708031566

2-Hydrazonophenylacetamides and thioacetamides derived from amides (or thioamides) and hydrazines N-monosubstituted are deprotonated by sodium hydride and acylated by methyl chloroformate. Spontaneous ring closure gives rise to the tetrahydro-1,2,4-triazine-3,5-diones and 5-thioxotetrahydro-1,2,4-triazin-3-ones. Under these conditions, chlorothioformylation of a 2-hydrazonophenylacetamide using thiophosgene leads to a 3-thioxotetrahydro-1,2,4-triazin-5-one. The transformation of the carbonyl groups into thiocarbonyl is described. Les 2-hydrazonophenylacetamides et thioacetamides derivant d'amides (ou de thioamides) et d'hydrazines N-monosubstitues sont deprotones par l'hydrure de sodium et acyles par le chloroformiate de methyle. Une reaction de cyclisation spontanee fournit alors les tetrahydro-1,2,4-triazine-3,5-diones et les 5-thioxotetrahydro-1,2,4-triazin-3-ones. Dans des conditions analogues, la chlorothioformylation d'un 2-hydrazonophenylacetamide par le thiophosgene conduit a une 3-thiox-otetrahydro-1,2,4-triazin-5-one. La thionation des fonctions carbonyle en thiocarbonyle est egalement decrite.

Full text of DOI:10.1080/10426509708031566

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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SYNTHESE DE TETRAHYDRO-1,2,4-
TRIAZINE-3,5-DIONES ET DE LEURS
HOMOLOGUES SOUFRES
M. J. Gil a , A. Reliquet a & J. C. Meslin a
a Laboratoire de Synthèse Organique , UMR C.N.R.S. 6513, 2, rue de la
Houssinière, 44072, Nantes, Cedex, France
Published online: 24 Sep 2006.
To cite this article: M. J. Gil , A. Reliquet & J. C. Meslin (1997) SYNTHESE DE TETRAHYDRO-1,2,4-
TRIAZINE-3,5-DIONES ET DE LEURS HOMOLOGUES SOUFRES, Phosphorus, Sulfur, and Silicon and the Related
Elements, 128:1, 105-117, DOI: 10.1080/10426509708031566
To link to this article: http://dx.doi.org/10.1080/10426509708031566
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