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

Author(s)

Ashraf, Abida ^{[1, 2]} ; Khalid, Muhammad ^[3] ; Tahir, Muhammad Nawaz ^[4] ; Yaqub, Muhammad ^[1] ; Naseer, Muhammad Moazzam ^[5] ; Kamal, Ghulam Mustafa ^[3] ; Saifullah, Bullo ^{[3, 6]} ; Braga, Ataualpa Albert Carmo ^[7] ; Shafiq, Zahid ^[1] ; Rauf, Waqar ^[8]

Affiliation

^[1] Bahauddin Zakariya Univ, Inst Chem Sci, Multan 60800 - Pakistan

^[2] Women Univ Multan, Dept Chem, Kutchery Campus, Multan 60000 - Pakistan

^[3] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan

^[4] Univ Sargodha, Dept Phys, Sargodha - Pakistan

^[5] Quaid I Azam Univ Islamabad, Dept Chem, Islamabad 45320 - Pakistan

^[6] Mehran Univ Engn Technol, Dept Biomed Engn, Jamshoro 76062, Sindh - Pakistan

^[7] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Ave Prof Lineu Prestes 748, BR-05508000 Sao Paulo - Brazil

^[8] Natl Inst Biotechnol & Genet Engn NIBGE, POB 577, Faisalabad - Pakistan

• Document type: Journal article
• Source: RSC ADVANCES; v. 9, n. 59, p. 34567-34580, OCT 27 2019.
• Web of Science Citations: 1

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,3 H)-dione (6a), 6-(5-fluoro-2-hydroxybenzoyl)-1-methylpyrido{[}2,3-d]pyrimidine-2,4(1H,3 H)-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(1 H,3H)-dione (6d). The chemical structures of the title compounds were ascertained by spectral techniques including H-1, C-13 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 (Delta E) 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. (AU)

• FAPESP's process: 11/07895-8 - Theoretical study of the Heck-Matsuda reactions
• Grantee: Ataualpa Albert Carmo Braga
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
• Grantee: Ataualpa Albert Carmo Braga
• Support Opportunities: Regular Research Grants