Article
Chemistry, Multidisciplinary
Wuji Sun, Xue Ma, Yuqi Pang, Lifeng Zhao, Qidi Zhong, Chunyan Liu, Qiangwen Fan
Summary: A green, simple and efficient method for the synthesis of quinazolin-4(3H)-ones has been developed via visible light-induced condensation cyclization. The method utilizes fluorescein as a photocatalyst and TBHP as a reaction promoter without the need for a metal catalyst. The reaction demonstrates high substrate tolerance and yields a variety of desired products in good to excellent yields. This method provides a straightforward strategy for the synthesis of quinazolin-4(3H)-ones.
Article
Chemistry, Multidisciplinary
Ali Akbari, Mahboobeh Zahedifar
Summary: The present study developed a new multi-component reaction for the synthesis of 2-aryl/alkyl-quinazolin-4(3H)-ones with good to excellent yields (86- 97%). The method utilized inexpensive and readily available starting materials and involved simple procedures and easy workup. Ammonium hexafluorophosphate (NH4PF6) was employed as an efficient reagent and catalyst. The synthesized compounds were characterized using 1H NMR and C-13 NMR techniques.
JOURNAL OF SAUDI CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Guanyu Zhou, Zhibin Huang, Xu Xu, Zhang Fang, Pengcheng Huang, Zefeng Deng, Bao Li, Yingsheng Zhao
Summary: A practical method using rhodium as the catalyst to synthesize quinoxalinones via intra/intermolecular amination has been developed, with a wide variety of products obtained in moderate to excellent yields. Gram-scale reactions were also achieved, highlighting the synthetic importance of this new transformation.
SYNTHESIS-STUTTGART
(2022)
Article
Biochemistry & Molecular Biology
Janez Mravljak, Lara Slavec, Martina Hrast, Matej Sova
Summary: Quinazolinones display diverse biological activities in medicinal chemistry. The study synthesized two series of 2-substituted quinazolin-4(3H)-ones and evaluated their antioxidant properties using three methods. The presence of hydroxyl groups or an ethylene linker enhanced antioxidant activity and led to metal-chelating properties in some derivatives.
Article
Chemistry, Organic
Yotsakorn Saebang, Vatcharin Rukachaisirikul, Juthanat Kaeobamrung
Summary: Two deoxyvasicinone analogues were synthesized via different linear cyclization processes from 2-(4-oxopentyl)quinazolin-4(3H)-ones. The first analogue, 1-acetyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one, was obtained through direct cyclization with I2 in basic conditions. The second analogue, 1-acetylpyrrolo[2,1-b]quinazolin-9(3H)-one, was synthesized via a two-step procedure involving geminal dichlorination in acidic conditions followed by intramolecular C-N bond formation in the presence of para-toluenesulfonic acid.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Ramaraju Korivi, Kanagaraj Madasamy, Popuri Sureshbabu, Subramaniyan Mannathan
Summary: An efficient and straightforward method for the synthesis of salicylanilide aryl and alkyl sulfonates from 1,2,3-benzotriazin-4(3H)-ones and organosulfonic acids is presented. The protocol is simple to perform and can be easily scaled up. It has a broad substrate scope with high tolerance towards functional groups, and provides the desired products in good to high yield. The application of the reaction is demonstrated by converting the desired product to salicylamides with high yields.
Article
Biochemistry & Molecular Biology
Maria Karelou, Dionysis Kampasis, Amalia D. Kalampaliki, Leentje Persoons, Andreas Kraemer, Dominique Schols, Stefan Knapp, Steven De Jonghe, Ioannis K. Kostakis, Sotiris S. Nikolaropoulos
Summary: Sixteen new 2-substituted quinazolines were synthesized and evaluated for their anti-proliferative activity against multiple cancer cell lines. Compound 17 showed remarkable activity against the majority of tested cell lines.
Article
Chemistry, Multidisciplinary
Gal Reddy Potuganti, Aravind Kandula, Kirti Vashishtha, Divakar Reddy Indukuri, Manjula Alla
Summary: A convenient one-pot method has been developed for the synthesis of fused pyrroloquinazolinone and amino quinazolinone derivatives. The method involves the in situ formation of 2-(2-bromophenyl)quinazolin-4(3H)-one and subsequent reaction with different amino acids/cyclic secondary amines under aerobic conditions. The protocol mediated by copper (II) salt results in the direct amination, decarboxylation, and cyclization to obtain polycyclic fused quinazolinone or aminated quinazolinone derivatives with satisfactory yields.
Article
Chemistry, Multidisciplinary
Apurba Dutta, Diganta Sarma
Summary: A metal, solvent and oxidant free method has been developed for the synthesis of quinazolin-4(3H)-ones under microwave irradiation. Using the same catalyst, 2,3-dihydroquinazolin-4(1H)-ones were also synthesized in water as a green and sustainable solvent. These protocols offer a simplistic and rapid approach for assembling diverse structural quinazolinones.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Article
Chemistry, Organic
Jiexiong Mai, Ziwei Huang, Shaohuan Lv, Quan Chen, Rongrong Chen, Feng Xie, Jun Wang, Bin Li
Summary: An efficient and visible light-promoted cascade N-alkylation/amidation reaction between quinazolin-4(3H)-ones and benzyl halides/allyl halides has been reported for the first time, providing a convenient approach for synthesizing quinazoline-2,4(1H, 3H)-diones. This cascade reaction shows good functional group tolerance and can also be applied to N-heterocycles such as benzo[d]thiazoles, benzo[d]imidazoles, and quinazolines. Control experiments reveal the crucial role of K2CO3 in this transformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Qing Tian, Jinli Zhang, Liang Xu, Yu Wei
Summary: An environmentally friendly electrochemical method was disclosed for the synthesis of quinazolin-4(3H)-one derivatives from readily available alpha-keto acids and 2-aminobenzamides. The decarboxylative cyclization process proceeds conveniently without the need for homogeneous metal catalysts, bases, or external oxidants. The protocol also features CO2 by-products, mild reaction conditions, and a wide variety of substrate scope, including an array of 2,3-disubstituted quinazolinone products.
MOLECULAR CATALYSIS
(2021)
Article
Spectroscopy
Tatyana N. Moshkina, Emiliya Nosova, Galina N. Lipunova, Marina S. Valova, Elizaveta F. Petrusevich, Robert Zalesny, Borys Osmialowski, Valery N. Charushin
Summary: 2-(2-Hydroxyphenyl)-3H-quinazolin-4-ones with diverse substituents on the phenol ring and their six-membered difluoroboron complexes were synthesized through a few-stage approach. The photophysical properties of these compounds were studied in two solvents and in the solid state, revealing the impact of substituents and substitution points on the photophysical properties of the dyes. In a THF/water mixture, all ligands showed enhanced emission with increasing water fraction due to aggregation-induced emission.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2021)
Article
Chemistry, Multidisciplinary
Mohanakumaran Athira, Suresh Snoxma Smile, Ponnusamy Shanmugam
Summary: An efficient method for constructing the quinazolinone skeleton has been achieved by catalyzing the reaction between 9-(phenylethynyl)-9H-fluoren-9-ols and substituted 2-aminobenzamides using boron trifluoride. The scope of this reaction has been demonstrated using various substrates. The reaction with NBS produced 2-(bromo(9H-fluoren-9-ylidene)methyl)-2-phenyl-2,3-dihydroquinazolin-4(1H)-one. The synthesized compounds have been structurally characterized and a plausible mechanism for their formation has been proposed. The synthetic utility of the products has been demonstrated through further reactions.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Le-Cheng Wang, Yu Zhang, Zhengkai Chen, Xiao-Feng Wu
Summary: A procedure for the palladium-catalyzed carbonylative reaction has been developed for the synthesis of pharmaceutically valuable 2-(trifluoromethyl)quinazolin-4(3H)-ones. The transformation uses Mo(CO)(6) as both a convenient CO source and a reducing reagent. This newly developed protocol is compatible with various nitro compounds and can be readily scaled up to a 1 mmol scale.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yibo Dong, Jinli Zhang, Jinchen Yang, Congcong Yan, Yangjie Wu
Summary: An efficient approach to quinazolin-4(3H)-ones was developed through a one-pot intermolecular annulation reaction, providing good functional group tolerance and high yields up to 98%. The control experiment showed that the thiol substrate can promote the dehydroaromatization step.
NEW JOURNAL OF CHEMISTRY
(2021)
