Selective Synthesis in Microdroplets of 2‐Phenyl‐2,3‐dihydrophthalazine‐1,4‐dione from Phenyl Hydrazine with Phthalic Anhydride or Phthalic Acid Academic Article uri icon

abstract

  • Pyridazine derivatives are privileged structures because of their potential biological and optical properties. Traditional synthetic methods usually require acid or base as a catalyst under reflux conditions with reaction times ranging from hours to a few days or require microwave assistance to induce the reaction. Herein, this work presents the accelerated synthesis of a pyridazine derivative, 2-phenyl-2,3-dihydrophthalazine-1,4-dione (PDHP), in electrosprayed microdroplets containing an equimolar mixture of phenyl hydrazine and phthalic anhydride or phthalic acid. This reaction occurred on the submillisecond timescale with good yield (over 90 % with the choice of solvent) without using an external catalyst at room temperature. In sharp contrast to the bulk reaction of obtaining a mixture of two products, the reaction in confined microdroplets yields only the important six-membered heterocyclic product PDHP. Results indicated that surface reactions in microdroplets with low pH values cause selectivity, acceleration, and high yields.

altmetric score

  • 0.25

author list (cited authors)

  • Gao, D., Jin, F., Yan, X., & Zare, R. N.

citation count

  • 8

publication date

  • December 2018

publisher