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

Autor(es)

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: RSC ADVANCES; v. 9, n. 59, p. 34567-34580, OCT 27 2019.
• Citações Web of Science: 0

Resumo

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)

• Processo FAPESP: 15/01491-3 - Estudo teórico das reações de acoplamento-cruzado: catálise homogênea e heterogênea
• Beneficiário: Ataualpa Albert Carmo Braga
• Linha de fomento: Auxílio à Pesquisa - Regular
• Processo FAPESP: 11/07895-8 - Estudo teórico das reações de Heck-Matsuda
• Beneficiário: Ataualpa Albert Carmo Braga
• Linha de fomento: Bolsas no Brasil - Pós-Doutorado
• Processo FAPESP: 14/25770-6 - Novas fronteiras em reações de acoplamento cruzado mediadas por paládio: associando catálise enantiosseletiva, ativações C-H, novos materiais e reações em fluxo visando alta eficiência e sustentabilidade em processos sintéticos
• Beneficiário: Carlos Roque Duarte Correia
• Linha de fomento: Auxílio à Pesquisa - Temático