19857-35-3Relevant academic research and scientific papers
One-pot solvent-free synthesis of 2, 3- disubstituted 4(3H)- quinazolinones catalyzed by long-chain double SO3H-functionalized Br?nsted acidic ionic liquids under microwave irradiation
Li, Xinzhong,Lin, Qi,Wang, Lefu
, p. 897 - 901 (2015)
A solvent-free approach for synthesis of 2, 3-disubstituted 4(3H)-quinazolinones by condensation of anthranilic acid with acyl chlorides and aromatic/aliphatic amines using two long chain double SO3H-functionalized acdic ionic liquids as catalyst under microwave irradiation was reported. Under optimized conditions, the reactions completed within 4-8 min and gave the target compounds in the yields of 76-94 %. Two ionic liquids could be recovered readily and recycled three times without any significant loss in their catalytic activity.
Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
, p. 5435 - 5441 (2020/08/03)
Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
Method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone
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Paragraph 0078-0082, (2019/11/12)
The invention discloses a method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone. According to the method, heteropolyacid ion liquid is taken as a catalyst, microwave heating and solvent-free synthesis technologies are utilized, and dihydroquinazolinone and quinazolinone derivatives are selectively synthesized through a 'one-pot-method' synthetic strategy with isatoic anhydride or derivatives of the isatoic anhydride, amine and aldehyde as raw materials. Compared with the prior art, the method has the multiple advantages that the efficiency is high, the costis low, environmental friendliness is realized, reaction selectivity is good, the product yield is high, selective synthesis can be realized, the catalyst is convenient to recover and apply, operationis easy, and industrial mass production is convenient, and the method is an environment-friendly efficient selective synthesis novel method and meets the environment-friendly and chemical developmentidea.
One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies
Cao, Liu,Huo, Hengrui,Zeng, Haipeng,Yu, Yu,Lu, Dengfu,Gong, Yuefa
supporting information, p. 4764 - 4773 (2018/11/10)
A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).
Design, synthesis and pharmacological evaluation of 2-phenyl quinazolin-4-one derivatives as anticolorectal cancer and anti-inflammatory agent
Bosco, Deena,Balakrishnan, Ashitha,Mishra, Rohan,Aneesh
, p. 2677 - 2685 (2018/11/20)
Quinazoline derivatives are heterocyclic compounds that acts as important structural lead for the discovery of effective therapeutic agents. The anti-inflammatory activity along with cytotoxicity helps to reduce the inflammation and pain associated with carcinoma. Derivatives of quinazoline-4-one were preliminary screened and in silico molecular modelling studies using Autodock were performed. In the docking study, ligands were docked against anticancer and anti-inflammatory targets. In silico analysis revealed that the compounds with aromatic substitution at 3rd and halogen substitution at 6th or 7th positions possess lesser side effects and have more potent antitumor activity. Based upon these results 12 compounds were selected, synthesized, characterized and screened for their in vitro, anti-inflammatory, antioxidant and anticancer activities. From the in vitro studies, compounds QA4, QA7 and QB1 showed good anticancer, anti-inflammatory and antioxidant activity when compared to the standard.
Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones
Qian, Chun,Liu, Kui,Tao, Shou-Wei,Zhang, Fang-Ling,Zhu, Yong-Ming,Yang, Shi-Lin
, p. 9201 - 9209 (2018/07/13)
A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.
Efficient and practical one-pot route to synthesise quinazolin4(3H)-ones using trifluoromethanesulfonic anhydride and 2-chloropyridine
Dadgar, Mohsen,Kalkhorani, Nasim Milani
, p. 120 - 122 (2015/06/16)
An effective, novel and rapid one-pot three-component route to quinazolin-4(3H)-ones from commercially available starting materials is described. Isatoic anhydride reacts with acyl chlorides and different amines using a combination of trifluoromethanesulf
Iron-catalyzed one-pot 2,3-diarylquinazolinone formation from 2-nitrobenzamides and alcohols
Wang, Huamin,Cao, Xiangxiang,Xiao, Fuhong,Liu, Saiwen,Deng, Guo-Jun
, p. 4900 - 4903 (2013/10/08)
A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reduct
Functionalized carbodiimide mediated synthesis of 2,3-disubstituted quinazolin-4(3 H)-ones via the tandem strategy of C-nucleophilic addition and intramolecular NH-substitution cyclization
Nakano, Hayato,Kutsumura, Noriki,Saito, Takao
, p. 3179 - 3184 (2012/11/14)
A facile synthesis of quinazolin-4(3H)-ones possessing carbon substituents at positions 2 and 3 has been developed. Key to the synthesis is a tandem strategy involving introduction of a 2-substituent and construction of the quinazolinone framework via C-nucleophilic addition to the carbodiimide cumulenic carbon followed by intramolecular nucleophilic substitution by the newly formed NH moiety at the proximal ester group.
One-pot three-component synthesis of 4(3 H)-quinazolinones from benzyl halides, isatoic anhydride, and primary amines
Adib, Mehdi,Sheikhi, Ehsan,Bijanzadeh, Hamid Reza
, p. 85 - 88 (2012/02/04)
A novel, one-pot, and three-component synthesis of 4(3H)-quinazolinones is described. Benzyl halides are oxidized to aldehydes under mild Kornblum conditions then undergo a three-component reaction with isatoic anhydride and primary amines to produce 4(3H)-quinazolinones in excellent yields. Georg Thieme Verlag Stuttgart. New York.
