BENZO[f][1,2,4]TRIAZINO[2,3-d][1,4]DIAZEPINES – A NEW HETEROCYCLIC SYSTEM: SYNTHESIS AND SPECTRAL CHARACTERISTICS
DOI:
https://doi.org/10.15421/jchemtech.v34i1.347428Keywords:
benzo[f][1,2,4]triazino[2,3-d][1,4]diazepines, acylation, cycle expansion, spectral data, X-Ray studyAbstract
Benzodiazepines are an important group of heterocyclic compounds in organic and medicinal chemistry due to their wide range of biological activity and application in medical practice, significant potential for functionalization and synthesis of various compounds with fused cycles. In this work, we present simple methods for the synthesis of a new system of benzo[f]1,2,4]triazino[2,3-d][1,4]diazepines by acylation of of 3-(2-aminophenyl)-6-R-1,2,4-triazine-5(2H)-ones with chloroacetyl chloride. The peculiarities of the reaction, the optimal conditions for the synthesis of the new heterocyclic system, namely the ratio of reagents, solvents, temperature and duration of the reaction, have been established. It has been shown that the starting compounds containing donor-acceptor groups in the reaction in question form a mixture of two structural isomers. An alternative synthetic method has been developed, namely nucleophilic ring expansion of the corresponding 3-R-6-chloromethyl-2H-[1,2,4]triazino[2,3-c]quinazolin-2-ones, and the probable mechanism of this reaction has been discussed. Structural confirmation was achieved using ¹H and ¹³C NMR, LS-MS and X-ray.
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