Polyethylene Glycol‐Bonded Tetraethyl Ammonium Hydroxide ([PEG‐TEA]OH): A New Surfactant‐Combined Base Catalyst for the Synthesis of 2,3‐Dihydroquinazolin‐4(1<i>H</i>)‐ones in Water

Safaei, Hamid Reza; Shekouhy, Mohsen; Ghorbanzadeh, Somayeh

doi:10.1002/slct.201800456

Cited by 8 publications

(13 citation statements)

References 85 publications

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“…Proton nuclear magnetic resonance spectra ( 1 H NMR) were obtained at 300, 400, and 500 MHz on Agilent spectrometers. 13 C NMR spectra were obtained at 75, 100, and 125 MHz on Agilent spectrometers. Spectra were recorded in DMSO-d 6 solutions.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The internal diameter of milling vessel was 5 cm with 200 mL capacity. The known compounds were characterized by comparing the melting points, 1 H and 13 C NMR with the reported compounds and the unknown compounds were characterized by melting point, IR, 1 H NMR, 13 C NMR, and HRMS analysis.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“… With such prominent physiological significance and pharmaceutical utility of the 2,3-dihydroquinazolin-4(1H)-one skeletons, it became utmost importance to synthesize quinazolinone-incorporating heterocycles. Several methodologies have been developed for the synthesis of quinazolinone derivatives during the past decade. − However with the growing concern of environmental contagions due to chemical pollutants, it became utmost necessary to develop alternative methods to perform organic synthesis under environmentally benign conditions aiming to reduce the Eco-scale for the chemical transformation and thus improve the “greenness” of the process. − Eliminating the VOC’s (Volatile Organic Component) in organic synthesis is one of the many tactics to achieve greenness in the process.…”

Section: Introductionmentioning

confidence: 99%

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Solvent-Free, Mechanochemically Scalable Synthesis of 2,3-Dihydroquinazolin-4(1H)-one Using Brønsted Acid Catalyst

Yashwantrao

Jejurkar

Kshatriya

et al. 2019

ACS Sustainable Chem. Eng.

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Although the synthesis of novel N-heterocyclic molecules is extremely demanding as well as challenging, the involvement of toxic solvents often triggers environmental safety concerns, resulting in process-engineering challenges. Herein, we have demonstrated a rapid, environmentally benign and energy efficient scalable method for the synthesis of 2,3-dihydroquinazolin-4(1H)-one by grinding in a mortar pestle as well as mechanochemically via ball milling using p-TSA catalyst. The ability to accomplish the reaction in the absence of solvent via grinding or milling with p-TSA catalyst, with an immediate reduction in the cost and operational procedures, features the significant advantages of this protocol. The scalability and significance of the operational parameters during mechanochemical milling in the tubular ball mill were also demonstrated. Excellent yield in short duration, large substrate scope, product scalability, and easy recoverability are the prime features of this mechanochemical solvent-free protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one. The study also demonstrated the significant role of ball diameter to improve the efficiency of the milling operation in this mechanochemical synthesis.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Solvent-Free, Mechanochemically Scalable Synthesis of 2,3-Dihydroquinazolin-4(1H)-one Using Brønsted Acid Catalyst

Yashwantrao

Jejurkar

Kshatriya

et al. 2019

ACS Sustainable Chem. Eng.

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“…在 CuI [62] 、CuCl 2 [63] 催化下, 邻溴苯甲酰胺可与芳香 [63] . 、胆碱 [67] 、聚乙二醇键合的四乙基氢氧化铵([PEG-TEA]OH) [68] 、氮杂环卡宾如 1,3-二丙基咪唑-2-亚基(NHC-PPIm) [69,70] 、大孔树脂 A26 OH (AA26OH) [71] 、金属改性的磺化硅胶 [72] 等.当醛参与反应时, 目标产物收率良好, 普遍在 85%～96%之间; 酮参与反应时, 产率稍低, 大多在 62%～93%之间. [67,68] ; 其二, 氮杂环卡宾类催化剂首先与羰基化合物作用生成两性的布雷斯洛(Breslow)中间体 IB, 然后 IB 与邻氨基苯甲腈中的氰基作用生成另一种两性离子 IIB, 随后 IIB 再关环脱去氮杂环卡宾的同时生成相应的噁嗪中间体 IIIB, 随后经分子内的 Dimroth 重排反应生成目标产物 IV (Path B) [69,70] .…”

Section: 以邻溴苯甲酰胺为底物unclassified

“…、胆碱 [67] 、聚乙二醇键合的四乙基氢氧化铵([PEG-TEA]OH) [68] 、氮杂环卡宾如 1,3-二丙基咪唑-2-亚基(NHC-PPIm) [69,70] 、大孔树脂 A26 OH (AA26OH) [71] 、金属改性的磺化硅胶 [72] 等.当醛参与反应时, 目标产物收率良好, 普遍在 85%～96%之间; 酮参与反应时, 产率稍低, 大多在 62%～93%之间. [67,68] ; 其二, 氮杂环卡宾类催化剂首先与羰基化合物作用生成两性的布雷斯洛(Breslow)中间体 IB, 然后 IB 与邻氨基苯甲腈中的氰基作用生成另一种两性离子 IIB, 随后 IIB 再关环脱去氮杂环卡宾的同时生成相应的噁嗪中间体 IIIB, 随后经分子内的 Dimroth 重排反应生成目标产物 IV (Path B) [69,70] . [73] .该方法反应条件温和, 绝大部分反应在 0.25～2 h 内能够完成, 目标产物收率在 39%～94%之间.不足之处在于所用原料之一的邻氨基 N-甲基-N-丙二烯基苯甲酰胺结构复杂、成本高且来源不便; 此外, 包括另一原料碘代烃在内的两种起始原料结构特殊, 多样性缺乏.…”

Section: 以邻溴苯甲酰胺为底物unclassified

Advances in Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

张晓鹏¹,

朱妍洁²,

朱奕崧³

et al. 2019

Chin. J. Org. Chem.

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2,3-Dihydroquinazolin-4(1H)-one compounds are an important class of nitrogen-containing fused heterocycles, which possess a wide range of pharmacological and biological activities and have important applications in the fields of synthesis and research & development of drugs. Therefore, its synthetic methods have also attracted considerable attention. In this paper, the main advances in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones and their proposed reaction mechanisms from the raw materials such as o-aminobenzamides, isatoic anhydrides, o-nitrobenzamides, o-azidobenzamide, o-bromobenzamide, o-bromobenzonitrile, o-aminobenzoic acids, o-aminobenzonitrile, o-amino-N-(propa-1,2-dienyl)benzamides, and N-alkyl anilines were introduced and reviewed, respectively. Finally, the synthesis of these compounds was summarized and the prospect of their development was prospected. Keywords 2,3-dihydroquinazolin-4(1H)-one; o-aminobenzamides; isatoic anhydrides; N-alkyl anilines; C-H activation & functionalization; palladium catalysis 2,3-二氢喹唑啉-4(1H)-酮是一类重要的含氮稠杂环化合物, 具有抗癌 [1～3] 、抗肿瘤 [4～6] 、治疗高血压 [7～9] 、抗炎 [10～12] 、抗菌 [13～15] 、利尿 [9,16,17] 、抗病毒 [18] 、抗痉挛 [19] 、抑制疟原虫增殖 [20] 、驱虫 [21] 、镇痛 [12] 等作用以及抑制组织蛋白酶 B&H [22] 、胆碱酯酶 [23,24] 、凝血因子 Xa [25] 、肌苷 5'-一磷酸脱氢酶 [26] 、蛋白激酶 C-θ [27] 、瞬时受体电位通道 M2 [28] 等广泛的药理及生物活性; 此外, 该类化合物也很容易被氧化成其喹唑啉-4(3H)-酮类似物, 后者通常作为重要模块用于构建天然产物 [29～31] 及药物分子 [32～34]. 由于 2,3-二氢喹啉-4(1H)-酮类化合物具有广泛且重要的生物活性及应用价值, 其合成方法也自然引起了人们的极大兴趣和关注.根据国内外的研究动态, 对其主要合成方法进行了总结.

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Designing, Synthesis, and Anti‐Breast Cancer Activity of a Series of New Quinazolin‐4(1H)‐one Derivatives

Reddy

Rajagopal

Naik

et al. 2022

Chemistry & Biodiversity

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The inhibition of phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha (PIK3CA) protein could be a promising treatment for breast cancer. In this regard, docking studies were accomplished on various functionalized organic molecules. Among them, several derivatives of quinazolin-4(1H)-one exhibited anti-breast cancer activity and satisfied the drug likeliness properties. Further, the in vitro inhibitory studies by a series of 2-(2-phenoxyquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-one molecules showed strong anti-cancer activity than the currently available drug, wortmannin. The MTT cytotoxicity assay was used to predict the anti-proliferative activity of these drugs against MCF-7 cancer cells by inhibiting the PIK3CA protein. The dose-dependent analysis showed a striking decrease in cancer cell viability at 24 h with inhibitory concentrations (IC 50 ) of 3b, 3c, 3d, 3f and 3m are 15 � 1, 17 � 1, 8 � 1, 10 � 1 and 60 � 1 (nanomoles), respectively. This is the first report in the literature on the inhibition of PIK3CA protein by quinazolinone derivatives that can be used in the treatment of cancer. Quinazolinone analogs have the potential to be safe and economically feasible scaffolds if they are produced using a chemical technique that is both straightforward and amenable to modification. From the cancer research perspective, this study can eventually offer better care for cancer patients.

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Polyethylene Glycol‐Bonded Tetraethyl Ammonium Hydroxide ([PEG‐TEA]OH): A New Surfactant‐Combined Base Catalyst for the Synthesis of 2,3‐Dihydroquinazolin‐4(1H)‐ones in Water

Cited by 8 publications

References 85 publications

Solvent-Free, Mechanochemically Scalable Synthesis of 2,3-Dihydroquinazolin-4(1H)-one Using Brønsted Acid Catalyst

Solvent-Free, Mechanochemically Scalable Synthesis of 2,3-Dihydroquinazolin-4(1H)-one Using Brønsted Acid Catalyst

Advances in Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Designing, Synthesis, and Anti‐Breast Cancer Activity of a Series of New Quinazolin‐4(1H)‐one Derivatives

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