Synthesis of N-substituted dibenzoazepine–pyridazine derivatives as potential neurologically active drugs

Abstract

Syntheses of pyridazine derivatives of dibenzoazepine, starting from N-substituted-dibenzoazepines, are reported here for the first time. In the reaction sequence, N-substitute dibenzoazepine derivatives were synthesized and then, examined inverse electron demand Diels–Alder (IEDDA) reactions between N-substituted dibenzoazepine derivatives and tetrazines. While in some reactions, targeted products were obtained using phenyliodo-bis(trifluoroacetate) (PIFA), in other reactions, they were obtained directly with tetrazines which also behaved as the oxidizing agent. Structures of these compounds were fully characterized by NMR, IR, and HRMS spectroscopic techniques.

Graphical Abstract

Keywords:

• Azepine
• 5H-dibenzo[b,f]azepine
• iminostilbene
• inverse electron demand Diels–Alder
• PIFA
• pyridazine
• tetrazine

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

The authors are grateful to Atatürk University for financial support.