3137-64-2Relevant articles and documents
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
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.
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 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.
