A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: synthesis, and structural, spectral and computational exploration

Abida Ashraf; Muhammad Khalid; Muhammad Nawaz Tahir; Muhammad Yaqub; Muhammad Moazzam Naseer; Ghulam Mustafa Kamal; Bullo Saifullah; Ataualpa Albert Carmo Braga; Zahid Shafiq; Waqar Rauf

doi:10.1039/C9RA05415D

A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: synthesis, and structural, spectral and computational exploration†

Abida Ashraf,^ae Muhammad Khalid,

*^b Muhammad Nawaz Tahir,^c Muhammad Yaqub,^a Muhammad Moazzam Naseer,

^d Ghulam Mustafa Kamal,^b Bullo Saifullah,

^bg Ataualpa Albert Carmo Braga,

^f Zahid Shafiq*^a and Waqar Rauf

^h

Author affiliations

* Corresponding authors

^a Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan
E-mail: zahidshafiq25@hotmail.com

^b Department of Chemistry, Khwaja Fareed University of Engineering & Information Technology, Rahim Yar Khan-64200, Pakistan
E-mail: muhammad.khalid@kfueit.edu.pk, Khalid@iq.usp.br

^c Department of Physics, University of Sargodha, Sargodha, Pakistan

^d Department of Chemistry Quaid-i-Azam University Islamabad, Pakistan

^e Department of Chemistry, Kutchery Campus, The Women University Multan, Multan 60000, Pakistan

^f Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Avenida Professor Lineu Prestes, 748, São Paulo 05508-000, Brazil

^g Department of Biomedical Engineering, Mehran University of Engineering Technology, Jamshoro, Sindh, Pakistan

^h National Institute of Biotechnology and Genetic Engineering (NIBGE), P. O. Box 577, Faisalabad, Pakistan

Abstract

In this work, we report the efficient synthesis of novel (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: 6-(2-hydroxy-5-methylbenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (6a), 6-(5-fluoro-2-hydroxybenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (6b), 6-(5-ethyl-2-hydroxybenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (6c) and 6-(2-hydroxy-5-isopropylbenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (6d). The chemical structures of the title compounds were ascertained by spectral techniques including ¹H, ¹³C NMR, UV-visible and FT-IR spectroscopy as well as single-crystal X-ray diffraction analysis. Additionally, density functional theory (DFT) and time-dependent (TD-DFT) computation were adopted to analyze the electronic structures of 6a–d. Compounds 6a–d were computed in the ground state for FT-IR spectroscopic and natural bond orbital (NBO) analysis by DFT/B3LYP with the 6-311+G(d,p) basis set. UV-vis spectroscopic and HOMO and LUMO energy values for 6a–d were determined via TD-DFT/B3LYP with the 6-311+G(d,p) basis set. The optimized geometric parameters, UV-vis findings, and vibrational frequencies indicate good consistency with the experimental data. NBO analysis was conducted to explore the interactions and charge transfer among different orbitals in the title compounds. The HOMO and LUMO band gap (ΔE) values for 6a–d were found to be 3.93, 3.91, 4.10 and 3.91 eV, respectively. Molecular electrostatic potential (MEP) analysis explored the reactivity of the title compounds by predicting their nucleophilic as well as electrophilic sites.

RSC Advances

A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: synthesis, and structural, spectral and computational exploration†

Abstract

Supplementary files

Article information

Download Citation

Permissions

A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: synthesis, and structural, spectral and computational exploration

Social activity

Search articles by author

Spotlight

Advertisements