Synthesis of 8,10-disubstituted-triazoloperimidines from (E)-3-(dimethylamino)-1-(8- phenyl-8H-[1,2,4]triazolo[4,3-a]perimidin-10-yl)prop-2-en-1-one and Their Antimicrobial Activity

Title:Synthesis of 8,10-disubstituted-triazoloperimidines from (E)-3-(dimethylamino)-1-(8- phenyl-8H-[1,2,4]triazolo[4,3-a]perimidin-10-yl)prop-2-en-1-one and Their Antimicrobial Activity

Volume: 15 Issue: 1

Author(s): Ghada S. Masaret and Thoraya A. Farghaly*

Affiliation:

• Department of Chemistry, Faculty of Science, Cairo University, Giza 12613,Egypt

Keywords: Enaminone, hydrazonoyl chlorides, pyridopyrimidines, pyrazoles, perimidines, antimicrobial agent.

Abstract: Aim and Objective: Enaminones belay to be extremely stable compounds and constitute a versatile group of salutary precursors for the synthesis of enormous classes of organic compounds. So, in this context, we synthesized a new enaminone, namely, (E)-3-(dimethylamino)-1-(8-phenyl-8H-[1,2,4]triazolo[4,3- a]perimidin-10-yl)prop-2-en-1-one (enaminone 2).

Materials and Methods: The reaction of enaminone 2 with different types of hydrazonoyl chlorides or hydrazine hydrate afforded new substituted pyrazoles. Also, the reaction of enaminone with 6-amino-2- thioxopyrimidin-4-one in acetic acid under reflux produced 2-thioxopyridopyrimidinone derivative. The latter thione derivative reacts with hydrazonoyl chlorides to give pyridotriazolopyrimidines. 5-(8-Phenyl-8H- [1,2,4]triazolo[4,3-a]perimidin-10-yl)isoxazole was produced from the reaction of enaminone 2 with hydroxylamine.

Results & Conclusion: The structure of all the novel perimidine derivatives was confirmed on the basis of spectral data and elemental analyses. The enaminone and the newly synthesized compounds were tested for their antimicrobial activity, and the results obtained revealed that some derivatives are more potent than the reference drugs used.

Cite this article as:

Masaret S. Ghada and Farghaly A. Thoraya *, Synthesis of 8,10-disubstituted-triazoloperimidines from (E)-3-(dimethylamino)-1-(8- phenyl-8H-[1,2,4]triazolo[4,3-a]perimidin-10-yl)prop-2-en-1-one and Their Antimicrobial Activity, Current Organic Synthesis 2018; 15 (1) . https://dx.doi.org/10.2174/1570179414666170601121137