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Quantum-chemical study of organic reaction mechanisms. XI. The interaction of diformylhydrazine with o- and p-aminophenols producing biologically active 4-substituted 1,2,4-triazoles
  • Elena Chirkina,
  • Ludmila Larina
Elena Chirkina
Irkutsk Scientific Center Siberian Branch of the Russian Academy of Sciences
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Ludmila Larina
Irkutsk Scientific Center Siberian Branch of the Russian Academy of Sciences
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Abstract

A mechanism for the reaction of diformylhydrazine with o- and p-aminophenols has been studied by quantum-chemical calculations within the framework of electron density functional theory using the B3LYP/6-311++G (d,p)//B2PLYP/6-311++G (d, p) basis sets. It is shown that the first stage of this reaction involves nucleophilic addition of the aminophenol nitrogen to one of the carbonyl groups of diformylhydrazine to afford an unstable geminal amino alcohol, which can be further dehydrated to iminohydrazide or hydrazonamide. The prototropic imino-amine rearrangement occurring in the iminohydrazide delivers hydrazonamide, The latter, owing to nucleophilic attack of the nitrogen atom at the second carbonyl group, is converted into a cyclic amino alcohol, dehydration of which produces the target 1,2,4-triazole. The obtained results have been compared with the data NMR spectroscopy.

Peer review status:UNDER REVIEW

01 Nov 2021Submitted to International Journal of Quantum Chemistry
02 Nov 2021Submission Checks Completed
02 Nov 2021Assigned to Editor
05 Nov 2021Reviewer(s) Assigned
05 Nov 2021Review(s) Completed, Editorial Evaluation Pending
05 Nov 2021Editorial Decision: Revise Minor
16 Nov 20211st Revision Received
17 Nov 2021Submission Checks Completed
17 Nov 2021Assigned to Editor
17 Nov 2021Reviewer(s) Assigned