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Vol. 35 No. 10 (2023): Vol 35 Issue 10, 2023

Copyright (c) 2023 DEVENDER, VISHNU, RAMULU , MURALIDHAR REDDY PUCHAKAYALA, KRISHNAM RAJU

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Facile Synthesis of Substituted 2-Styrylnaphthyridine and its Derivatives via sp3 C-H Functionalization under Mild Conditions and their Antimicrobial Activity

https://doi.org/10.14233/ajchem.2023.29067
DEVENDER KOTHULA
Department of Chemistry, University College of Technology, Osmania University, Hyderabad-500007, Telangana State, India
https://orcid.org/0009-0000-6902-3911
VISHNU THUMMA
Department of Sciences and Humanities, Matrusri Engineering College, Hyderabad-500059, Telangana State, India.
https://orcid.org/0000-0001-6830-3671
RAMULU DHANAVATH
Department of Chemistry, University College of Technology, Osmania University, Hyderabad-500007, Telangana State, India.
https://orcid.org/0009-0002-1961-5569
MURALIDHAR REDDY PUCHAKAYALA
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, Telangana State, India.
https://orcid.org/0000-0001-8407-7985
KRISHNAM RAJU
Department of Chemistry, University College of Technology, Osmania University, Hyderabad-500007, Telangana State, India.
https://orcid.org/0000-0001-7615-4848

Corresponding Author(s) : MURALIDHAR REDDY PUCHAKAYALA

pmdreddy@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 10 (2023): Vol 35 Issue 10, 2023

Abstract

A simple, metal free strategy is described for the synthesis of substituted 2-styryl-1,8-naphthyridines and pyrazole, imidazopyridine based styryl conjugates under basic mild conditions (piperidine in ethanol) at 70 ºC. The reaction progressed via sp3 C-H functionalization of substituted methyl-1,8-naphthyridines with various aromatic, heteroaromatic aldehyde substrates by Knoevenagel condensation to provides functionalized pyrazole, imidazopyridine based styryl-1,8-naphthyridines in good to excellent yields (85-95%) at impressive reaction time. This approach involves a common organocatalyst, cheap starting materials and shorter reaction times. An extensive variability of substrates was tolerated well to afford the desired products. Furtherly, all the synthesized derivatives were tested for their biological activity, i.e., antibacterial and antifungal. In tested series, compounds 3c, 3d, 3e, 3i, 3k, 3l, 4c, 4d and 4f established excellent inhibition zone of activity against standard drugs.

Keywords

1,8-Naphthyridines Knoevenagel condensation Ogranocatalyst Antibacterial Antifungal
KOTHULA, D., THUMMA, V., DHANAVATH, R., PUCHAKAYALA, M. R., & ATCHA, K. R. (2023). Facile Synthesis of Substituted 2-Styrylnaphthyridine and its Derivatives via sp3 C-H Functionalization under Mild Conditions and their Antimicrobial Activity. Asian Journal of Chemistry, 35(10), 2527–2536. https://doi.org/10.14233/ajchem.2023.29067
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