3137-64-2Relevant academic research and scientific papers
Aziridination of α,β-unsaturated esters bearing allylic hydroxy groups with 3-acetoxyaminoquinazolinones: Evidence for a mechanism comprising Michael addition-SN2 nucleophilic displacement of acetoxy for aziridination of α,β-unsaturated esters
Atkinson, Robert S.,Williams, Paul J.
, p. 1951 - 1959 (1996)
Aziridinations of the allylic alcohol-bearing α,β-unsaturated esters 6 and 7 and their corresponding acetates 8 and 9 have been carried out under standard conditions using 3-acetoxyaminoquinazolinone 2. Whereas the preferred sense of diastereoselectivity
Substrate-controlled diastereoselective aziridination of alkenes using 3-acetoxyaminoquinazolinone in the presence of hexamethyldisilazane
Ulukanli, Sabri,Karabuga, Semistan,Celik, Ayhan,Kazaz, Cavit
, p. 197 - 199 (2005)
8-Phenylmenthol derived α,β-unsaturated esters were aziridinated highly diastereoselectively using 3-acetoxyamino-2-ethylquinazolinone. The yields of these aziridines were greatly improved in the presence of hexamethyldisilazane.
Aziridination of Electron-rich Acyclic Allylic alcohols using 3-Acetoxyaminoquinazolinones
Atkinson, Robert S.,Fawcett, John,Russell, David R.,Williams, Paul J.
, p. 3241 - 3244 (1995)
The products from aziridination of the phenyl-substituted allylic alcohols 6 and 7 with 3-acetoxyaminoquinazolinones 1 and 15 have been compared with those from aziridination of the methyl ester analogues 2, and 3: the differences in diastereoselectivities using these electron-rich and electron-deficient alkenes are ascribed to the intervention of transition states 8 and 4 respectively.
AZIRIDINATION OF ALKENES BY 3-AMINO-2-ETHYLQUINAZOLIN-3H-4-ONE AND LEAD TETRA-ACETATE-TRIFLUOROACETIC ACID
Atkinson, Robert S.,Darrah, Christine M.,Kelly, Brian J.
, p. 1711 - 1712 (1987)
A number of alkenes undergo aziridination in good yield by oxidative addition of the title N-aminoquinazolone (1) only in the presence of TFA.
Imination of sulfoxides using 3-acetoxyaminoquinazolinone as nitrogen source in the presence of hexamethyldisilazane
Karabuga, Semistan,Kazaz, Cavit,Kilic, Hamdullah,Ulukanli, Sabri,Celik, Ayhan
, p. 5225 - 5227 (2005)
The reaction of 3-acetoxyaminoquinazolinone (QNHOAc) with various sulfoxides in the presence of HMDS as an acetic acid scavenger, afforded the corresponding sulfoximides in good yields. Sulfoximidation of phenyl methyl sulfoxide using a Q*NHOAc having a s
Visible-light- And bromide-mediated photoredox Minisci alkylation of N-heteroarenes with ester acetates
Deng, Guo-Jun,Huang, Huawen,Shi, Hang,Wang, Chunlian
supporting information, p. 9177 - 9181 (2021/11/16)
A visible-light-induced photoredox Minisci alkylation reaction of N-heteroarenes with ethyl acetate has been reported. The low-toxic ethyl acetate was used for the first time as an alkylation reagent. Hence, 4-quinazolinones, quinolines and pyridines reacted smoothly in the current reaction system. Mechanistic studies indicate that LiBr plays a key role to dramatically improve the efficiency of the reaction by the mediation of hydrogen atom transfer. This journal is
Synthesis and in vitro antileishmanial efficacy of novel quinazolinone derivatives
Prinsloo, Izak F.,Zuma, Nonkululeko H.,Aucamp, Janine,N’Da, David D.
, p. 383 - 398 (2020/09/23)
Currently available drugs being used to treat leishmaniasis have several shortcomings, including high toxicity, drug administration that requires hospitalization, and the emergence of parasite resistance against clinically used drugs. As a result, there is a dire need for the development of new antileishmanial drugs that are safe, affordable, and efficient. In this study, two new series of synthesized quinazolinone derivatives were investigated as potential future antileishmanial agents, by assessing their activities against the Leishmania (L.) donovani and L.?major species. The cytotoxicity profiles of these derivatives were assessed in vitro on Vero cells. The compounds were found to be safer and without any toxic activities against mammalian cells, compared to the reference drug, halofuginone, a clinical derivative of febrifugine. However, they had demonstrated poor antileishmanial growth inhibition efficacies. The two compounds that had been found the most active were the mono quinazolinone 2d and the bisquinazolinone 5b with growth inhibitory efficacies of 35% and 29% for the L.?major and L.?donovani 9515 promastigotes, respectively. These outcomes had suggested structural redesign, inter alia the inclusion of polar groups on the quinazolinone ring, to potentially generate novel quinazolinone derivatives, endowed with effective antileishmanial potential.
Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions
Xie, Zongbo,Lan, Jin,Zhu, Haibo,Lei, Gaoyi,Jiang, Guofang,Le, Zhanggao
supporting information, p. 1427 - 1431 (2020/11/02)
A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.
Cobalt-Catalyzed Tandem Transformation of 2-Aminobenzonitriles to Quinazolinones Using Hydration and Dehydrogenative Coupling Strategy
Samim, Sk. Abdus,Roy, Bivas Chandra,Nayak, Sourav,Kundu, Sabuj
, p. 11359 - 11367 (2020/10/12)
A tandem synthesis of quinazolinones from 2-aminobenzonitriles is demonstrated here by using an aliphatic alcohol-water system. For this transformation, a cheap and easily available cobalt salt and P(CH2CH2PPh2)3 (PP3) ligand were employed. The substrate scope, scalability, and synthesis of natural products exhibited the vitality of this protocol.
Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives
Dai, Zeshu,Li, Dan,Li, Zhiyao,Liu, Heng,Luo, Wen,Shang, Suqin,Tian, Qingqiang,Wang, Shuqi,Wang, Xuetong,Wang, Yin,Wu, Huili,Xiao, Xin,Yuan, Jianyong,Zhou, Shangjun
, (2020/09/10)
Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.
