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- Title
Azomalonate Syntheses Part II. Synthesis and Reactivity of Novel 1,2,4-Triazin-5-one Derivatives.
- Authors
Heckendorn, Roland
- Abstract
Base treatment of azomalonates derived from N-substituted dialkyl (2-chloroacetamido)malonates results in the formation of 4-substituted alkyl 5-oxo-1,4,5,6-tetrahydro-1,2,4-triazine-3-carboxylates. The same malonates coupled with diazotized 2-amino-5-chlorobenzophenone or methyl anthranilate afford triazinones which can be cyclized into novel triazino[1,6- a]indoles. Two representative heterocycles are further characterized by typical reactions. Whereas oxidation gives the corresponding triazine-5,6-diones, the outcome of the reduction is strongly dependent on the nature of the substituent at C(4). Bromination followed by aqueous workup leads to the 6-hydroxy derivatives. Some mechanistic aspects of this novel triazinone synthesis are discussed.
- Publication
Helvetica Chimica Acta, 1990, Vol 73, Issue 6, p1700
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19900730615