A Multifield Study on Dimethyl Acetylenedicarboxylate: A Reagent Able to Build a New Cycle on Diaminoimidazoles

Molecules. 2022 May 22;27(10):3326. doi: 10.3390/molecules27103326.

Abstract

A new effective method for the synthesis of imidazo[1,5-b]pyridazines derivatives (yields = 68-89%) by the interaction of 1,2-diamino-4-phenylimidazole with DMAD, in methanol and in the presence of a catalytic amount of acetic acid, is proposed. The course of reaction has been examined by classical organic methods, HPLC-MS analysis, and quantum-chemical calculations.

Keywords: DFT calculations; dimethyl acetylenedicarboxylate; imidazo[1,5-b]pyridazines.

MeSH terms

  • Alkynes*
  • Catalysis
  • Indicators and Reagents
  • Pyridazines*

Substances

  • Alkynes
  • Indicators and Reagents
  • Pyridazines
  • acetylenedicarboxylic acid dimethyl ester