Abstract
Thiophene-substituted chalcones were cyclised with guanidine in the presence of potassium hydroxide to get 4-substituted-6-thiophenopyrimidines 2a–e which were then refluxed with acetylacetone to obtain pyrimidopyrimidines 3a–e. Compounds 2a–e were also refluxed with ethylacetoacetate to afford pyirmidopyirimidines 4a–e which on refluxing with POCl3 in presence of DMF produced compounds 5a–e. Nucleophilic substitution reactions on 5a-e were carried out with aniline to obtain 6a-e. The structures of the newly synthesised compounds have been confirmed by elemental analysis and spectral studies. Some selected compounds have been screened for antibacterial and analgesic activities.
Thiophene-substituted chalcones were cyclised with guanidine to obtain 4-substituted-6-thiophenopyrimidines 2a-e which were refluxed with acetylacetone to obtain pyrimidopyrimidines 3a-e. Compounds 2a-e were refluxed with ethylacetoacetate to afford pyirmidopyirimidines 4a-e which on refluxing with POCl3 in presence of DMF produced compounds 5a-e. Nucleophilic substitution reactions on 5a-e produced compounds 6a-e.
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Acknowledgements
Authors are thankful to the Principal, Sahyadri Science College (Autonomous), Shimoga and the Chairman, Department of Chemistry, Sahyadri Science College (Autonomous), Shimoga, for providing necessary laboratory facilities. Authors are also thankful to the Principal, SCS College of Pharmacy, Harapanahalli, for providing facilities to conduct biological activities.
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Structural data (NMR, IR, mass and elemental analysis) of the rest of the compounds are provided in the supplementary information file. The electronic supporting information can be seen at www.ias.ac.in/chemsci.
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SIDDESH, M.B., PADMASHALI, B., THRIVENI, K. et al. Synthesis of thiophene-linked pyrimidopyrimidines as pharmaceutical leads. J Chem Sci 126, 821–826 (2014). https://doi.org/10.1007/s12039-014-0614-z
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DOI: https://doi.org/10.1007/s12039-014-0614-z