156635-75-5Relevant academic research and scientific papers
Synthesis of 4(pyrazol-3-yl)[1,2,4]triazolo[4,3-a]quinoxalines and tetrazolo analog
Atta,El-Massry,Hamid,El Ashry,Amer
, p. 549 - 552 (1994)
The transformation of 2-chloro-3-[5-(acetoxymethyl)-1-phenylpyrazol-3-yl]quinoxaline 3 to 1-aryl-4-[5-(hydroxymethyl-1-phenylpyrazol-3-yl][1,2,4]triazolo[4,3-a] quinoxalines 4a-c has been achieved upon treatment with aroylhydrazines in boiling butanol. Compounds 4a-c were smoothly acetylated by acetic anhydride to give their acetyl derivatives 5a-c in good yield. 4-[5-(Acetoxymethyl)-1-phenylpyrazol-3-yl]1-methyl[ 1,2,4]triazolo[4,3-a]quinoxaline was prepared by ring closure of 2-hydrazine-3-[5-(hydroxymethyl)-1-phenylpyrazol-3-yl]quinoxaline 6 by the action of acetic anhydride. The reaction of 6 with acetylacetone afforded 3-[5-(hydroxymethyl)-1-phenylpyrazol-3-yl]-2-(3,5-dimethylpyrazol-1-yl )quinoxaline 8. In addition, the reaction of 3 with sodium, azide in boiling N,N-dimethylformamide yielded the fused tetrazolo[1,5-a]quinoxaline 9.
Synthesis and characterisation of triazolo- And pyrazol-3-yl quinoxaline derivatives from dehydro-L-ascorbic acid hydrazone and their antimicrobial activity
El-Sekily,Mancy,El-Sekely
, p. 641 - 649 (2020/07/02)
The 4-(pyrazol-3-yl)[1,2,4]triazolo[4,3-a]quinoxaline derivatives 4a-c were prepared by the reaction of 2-chloro-3-[5-(acetoxymethyl)-1-phenylpyrazol-3-yl]quinoxaline 2 with aroylhydrazines in ethanol followed by boiling the resulted products in butanol. Acetylation of 4a-c with boiling acetic anhydride, afforded the acetyl derivatives 5a-c. Treatment of 2 with thiosemicarbazide, afforded the quinoxaline hydrazinothiosemicarboxamide 6 which upon acetylation with boiling acetic anhydride, gave (1,2-dihydro-3-methyl-5H-5-thio-1,2,4-triazol-3-yl)-3-[5-(acetoxymethyl)-1-phenylpyrazol-3-yl]quinoxaline 7. Compound 2 reacted with sodium methoxide or sodium ethoxide, to produce the alkoxy derivatives 8a,b. Furthermore, treatment of 2 with hydrazine hydrate, gave the 2-hydrazino derivative 9 which upon treatment with arylaldehydes, gave the arylhydrazones 10a-e which were transformed to 1-aryl-4-[5-(hydroxymethyl)-1-phenylpyrazol-3-yl][1,2,4]triazolo[4,3-a] quinoxalines 11a-c and acetylated to 12a-c compound 9 which when reacted with β-naphthylglyoxal produced 13. It was also acetylated to 14. Similarly, compound 9 reacted with ethylacetoacetate giving 15 and was acetylated to 16. Some of the novel quinoxaline derivatives were subjected to in vitro antimicrobial screening.
