16347-56-1Relevant articles and documents
Microwave-assisted [3+2] cycloaddition and suzuki-miyaura cross-coupling for a concise access to polyaromatic scaffolds
Hedou, Damien,Deau, Emmanuel,Dubouilh-Benard, Carole,Sanselme, Morgane,Martinet, Anthony,Chosson, Elizabeth,Levacher, Vincent,Besson, Thierry
, p. 7533 - 7545 (2013)
Novel 3-(prop-2-ynyl)pyrido[2,3-d]pyrimidin-4(3H)-ones and 3-(prop-2-ynyl)quinazolin-4(3H)-ones have been synthesized in a high-yielding microwave-assisted one-pot procedure. The one-pot sequence was conveniently extended to the synthesis of commercially unavailable 6-bromo-N 3-propargylpyrido[2,3-d]pyrimidinone by a regiocontrolled bromination with NBS. The synthetic scaffolds were successfully converted into triazoles by copper(I)-catalyzed [3+2] cycloaddition and substituted at the 6-position by Suzuki-Miyaura cross-coupling in high overall yields. A microwave-assisted one-pot sequential synthesis involving esterification, formylation, bromination, and cyclization of anthranilic and 2-aminonicotinic acid derivatives provides access to N3-propargylquinazolinones or -pyridopyrimidinones in high overall yields. Functionalization by [3+2] cycloaddition and Suzuki-Miyaura cross-coupling rapidly led to 48 novel polyaromatic heterocycles.
Visible-light induced copper(i)-catalyzed oxidative cyclization of: O -aminobenzamides with methanol and ethanol via HAT
Bhargava Reddy, Mandapati,Prasanth, Kesavan,Anandhan, Ramasamy
, p. 9601 - 9605 (2020/12/28)
The use of the in situ generated ligand-copper superoxo complex absorbing light energy to activate the alpha C(sp3)-H of MeOH and EtOH via the hydrogen atom transfer (HAT) process for the synthesis of quinazolinones by oxidative cyclization of alcohols with o-aminobenzamide has been investigated. The synthetic utility of this protocol offers an efficient synthesis of a quinazolinone intermediate for erlotinb (anti-cancer agent) and 30 examples were reported.
Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones
He, Junhui,Dong, Jianyu,Su, Lebin,Wu, Shaofeng,Liu, Lixin,Yin, Shuang-Feng,Zhou, Yongbo
supporting information, p. 2522 - 2526 (2020/04/09)
A selective functionalization of C-C-C bonds toward N-C-O bonds is realized by an n-Bu4NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant. The systematic process involves oxygenation, nitrogenation, ring-opening, and recyclization, affording a broad range of quinazolinones in good to excellent yields.