Abstract
Background: pyrazolo[3',4':4,5]pyrimido[1,6-b][1,2,4]-triazines have been found to possess a wide range of medical activities.
Objective: we interested to synthesis a new series of pyrazolo[3',4':4,5]pyrimido[1,6-b][1,2,4]triazines via the reaction of 1,3-diphenyl-4-hydrazino-pyrazolo[3,4-d]pyrimidine with ethyl aroyl pyrovates and invistigate thier antimicrobial activity. Not only the biological activity is our aim but also, to elucidate the actual tautomeric structure of the products.
Method: A new series of pyrazolo[3',4':4,5]pyrimido[1,6-b][1,2,4]triazine derivatives was prepared via condensation of ethyl aroylpyruvates with 1,3-diphenyl-4-hydrazino-pyrazolo[3,4-d]pyrimidine. Also, treatment of these compounds with hydrazine hydrate afforded a new series of 1,3-diphenyl-4-(7-aryl-2,6-dihydropyridazino[ 3,4-e][1,2,4]triazin-3-yl)-1H-pyrazol-5-amine.
Results: The mechanism of the reaction was discussed and proved to proceed via Dimroth rearrangement. The structure of all the newly synthesized compounds was established on the basis of spectral data and elemental analysis. The antimicrobial activity of the products was screened and some derivatives showed promising activities against the used bacteria and fungi species.
Conclusion: We success in synthesis of a new series of bioactive pyrazolo[3',4':4,5]pyrimido[1,6-b][1,2,4]triazines and elucidation of their actual structure.
Keywords: Ethyl aroylpyruvates, Dimroth rearrangement, pyrazolo[3', 4':4, 5]-pyrimido[1, 6-b][1, 2, 4]triazine, antimicrobial activity, 4- hydrazinopyrazolo[3, 4-d]pyrimidine.
Graphical Abstract
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
17
3
2
2