27259-73-0Relevant academic research and scientific papers
A new fluorescent probe for ultrasensitive detection of phosgene in solution and the gas phase
Zeng, Fenfen,Bao, Guangbo,Zhou, Baocheng,Han, Yifeng
, p. 5631 - 5636 (2021)
Due to the high toxicity and commercial availability of phosgene, it is urgent to detect phosgene quickly and reliably to deal with its potential serious threat to public safety. A new 2-(2-aminophenyl)quinazolin-4(3H)-one (APQ) based fluorescent probeAPQhas been developed as a rapid, highly sensitive, and selective sensor for phosgene in this work.APQdisplays very weak fluorescence in acetonitrile due to the free rotation of the 2-aminophenyl moiety. After reacting with phosgene,APQis converted to a new restricted intramolecular motion productAPQU1. Owing to the specific cyclization reactions,APQexhibits an obvious fluorescence response toward phosgene with a large Stokes shift (104 nm), instant response (less than 20 s), and low detection limit (0.16 ppm). Moreover, theAPQ-loaded test strip was prepared and demonstrated to have practical utility in detecting phosgene vapor.
N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols
Anandaraj, Pennamuthiriyan,Kamatchi, Thangavel Sathiya,Ramesh, Rengan
, (2022/01/11)
New Pincer type Pd(II) complex [Pd(NNO)(PPh3)] (1) prompted synthesis of quinazolinones via dehydrogenative coupling of readily accessible alcohols, and o-aminobenzamide is described. A diverse range of quinazolinones has been synthesized efficiently with good to excellent yields employing low catalyst loading (0.5 mol%) under the aerobic condition without any additives/oxidants. A plausible mechanism for the construction of quinazolinones has been proposed via cyclic aminal intermediate. Large-scale synthesis attests to the productiveness of the current strategy.
Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3 H)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide
Balaji, Sundarraman,Balamurugan, Gunasekaran,Ramesh, Rengan,Semeril, David
, p. 725 - 734 (2021/04/06)
A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation of the complexes has been recognized by analytical and spectral methods (FT-IR, NMR, HR-MS). The presence of a square-planar geometry around the palladium(II) ion was confirmed by single crystal X-ray diffraction study. A wide range of substituted quinazolinones have been successfully achieved from a diverse range of benzyl alcohols in good to excellent yields using 1.0 mol % of catalyst loading under aerobic conditions. Furthermore, control experiments reveal that the dehydrogenative coupling reaction involves initially the formation of an aldehyde intermediate and subsequent formation of a cyclic aminal intermediate.
A microwave-assisted copper-mediated tandem approach for fused quinazoline derivatives
Malasala, Satyaveni,Polomoni, Anusha,Chelli, Sai Manohar,Kar, Swayamsidda,Madhavi,Nanduri, Srinivas
supporting information, p. 1854 - 1859 (2021/03/14)
A method for the microwave-assisted copper-mediated oxidative coupling reaction of different aldehydes and quinazolines/benzimidazoles has been developed for the synthesis of fused-polycyclic systemsvianew C-N bond formation. The current methodology involves the use of environmentally benign NH4OAc as the amine source in the presence of 2-propanol as the solvent. This novel tandem reaction approach offers a rapid and straightforward access to complex fused quinazoline derivatives in an efficient manner.
Luotonin A and Its Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents
Hao, Yanan,Liu, Yuxiu,Ma, Dejun,Wang, Kaihua,Wang, Qingmin,Wang, Ziwen
, p. 8764 - 8773 (2020/09/16)
Plant diseases caused by viruses and fungi have posed a serious threat to global agricultural production. The discovery of new leads based on natural products is an important way to innovate pesticides. In this work, natural product luotonin A was found to have good antiviral activity against tobacco mosaic virus (TMV) for the first time. A series of luotonin A derivatives were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities systematically. Most compounds displayed better antiviral activities against TMV than commercial ribavirin. Compounds 9k, 12b, and 12d displayed about similar inhibitory effects as ningnanmycin (inhibitory rates of 55, 57, and 59% at 500 μg/mL for inactivation, curative, and protection activities in vivo, respectively), the best antiviral agent at present, and emerged as novel antiviral leads for further research. We selected 9k for further antiviral mechanism research via transmission electron microscopy and molecular docking, which revealed that compound 9k can interact with TMV coat protein through the hydrogen bond, leading to its polymerization, thus preventing virus assembly. Further fungicidal activity tests showed that these compounds also showed broad-spectrum fungicidal activities against 14 kinds of phytopathogenic fungi. Especially, compound 14 with a 100% antifungal effect against Botrytis cinereal emerged as a lead for further research. This work provides a reference for the development of agricultural active ingredients based on Chinese medicine plants.
Method for photocatalytic synthesis of quinazolinone compound in aqueous phase (by machine translation)
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Paragraph 0030; 0031; 0032; 0033; 0040; 0041, (2020/11/22)
The method comprises the following steps: taking the compound of the formula (I) and the compound of the formula (II) as a solvent, adding a photocatalyst and a phase transfer catalyst to obtain the quinazolinone compound (III) under the condition of alkali and visible light. Compared with the prior art, the method not only can be applied to a large amount of functional groups, has high yield, few byproducts, and is simple and safe to operate, low in cost and environment-friendly. Wherein R is hydrogen or R1 Is H, C1 - C4 alkoxy, halogen or nitro; R2 Is H, substituted or unsubstituted phenyl, 2 - pyridyl or 2 - thienyl; the substituted phenyl is phenyl substituted by amino, nitro, C1 - C4 alkyl or C1 - C4 alkoxy. (by machine translation)
Method for synthesizing quinazolinone compound by photo-catalyzing alcohol oxidation in water phase
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Paragraph 0028-0031; 0038-0039, (2020/10/29)
The invention discloses a method for synthesizing a quinazolinone compound by photo-catalyzing alcohol oxidation in a water phase, which comprises the following steps: by taking a compound shown as aformula (I) and a compound shown as a formula (II) as raw materials and water as a solvent, adding a visible light catalyst, and reacting under the conditions of alkali and visible light to obtain a quinazolinone compound (III). The method for preparing the quinazolinone compound is environmentally friendly, easy and convenient to operate, safe, cheap and efficient. Compared with the prior art, the method is applicable to a large number of functional groups, high in yield, few in byproducts, simple and safe to operate, low in cost and environment-friendly; wherein R1 is H, C1-C4 alkoxy, halogen or nitro; and R2 is H, substituted or unsubstituted phenyl, 2-pyridyl, 2-thienyl or 5-methylfuryl.
Lewis-Acid-Catalysed Activation of Nitriles: A Microwave-Assisted Solvent-Free Synthesis of 2,4-Disubstituted Quinazolines and 1,3-Diazaspiro[5.5]undec-1-enes
Saikia, Ujwal Pratim,Borah, Geetika,Pahari, Pallab
supporting information, p. 1211 - 1217 (2018/03/21)
Two different modes of cyclization take place to synthesize quinazoline, quinazolinone, and 1,3-diazaspiro[5.5]undec-1-ene derivatives through the Lewis-acid-catalysed activation of both aliphatic and aromatic nitriles in a single-step, solvent-free, and transition-metal-free reaction. An amidine is expected to form as an intermediate; this then undergoes intramolecular cyclization in a one-pot reaction sequence. The reaction is carried out under microwave irradiation using trimethylsilyltrifluoromethane sulfonate (TMSOTf) as a catalyst and nitriles as a nitrogen source with the respective reaction partners.
An Efficient One-Pot Multicomponent Synthesis of Tetracyclic Quinazolino[4,3- b ]quinazolines by Sequential C-N Bond Formation and Copper-Mediated Aerobic Oxidative Cyclization
Potuganti, Gal Reddy,Indukuri, Divakar Reddy,Alla, Manjula
supporting information, p. 1717 - 1722 (2018/05/28)
An efficient one-pot synthesis of quinazolino[4,3- b ]quinazoline derivatives has been accomplished, starting from 2-(2-bromophenyl)quinazolin-4(3 H)-one, aldehydes, and various nitrogen sources under aerobic conditions. The multicomponent protocol is med
Synthesis of Quinazolin-4(3 H)-ones via the Reaction of 2-Halobenzamides with Nitriles
Yu, Xiaoqiang,Gao, Linqi,Jia, Linan,Yamamoto, Yoshinori,Bao, Ming
, p. 10352 - 10358 (2018/09/18)
This paper describes a convenient method to synthesize quinazolin-4(3H)-ones from simple and readily available 2-halobenzamides and nitriles. The Lewis acid Cu-catalyzed nucleophilic addition of 2-halobenzamide to nitriles followed by SNAr reaction proceeds smoothly in the presence of tBuOK as a base to produce quinazolinone derivatives.
