50498-61-8Relevant academic research and scientific papers
Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
Peng, Jin-Bao,Geng, Hui-Qing,Wang, Wei,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
, p. 10 - 13 (2018/07/03)
A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted both as a solid CO source and a reductant. Notably, methaqualone as a sedative and hypnotic medication can be prepared easily in 68% yield (4b) under our conditions as well.
Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization
Hirai, Motohiro,Terada, Shumpei,Yoshida, Hiroaki,Ebine, Kenki,Hirata, Tomoaki,Kitagawa, Osamu
supporting information, p. 5700 - 5703 (2016/11/17)
In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmet
Functionalized carbodiimide mediated synthesis of 2,3-disubstituted quinazolin-4(3 H)-ones via the tandem strategy of C-nucleophilic addition and intramolecular NH-substitution cyclization
Nakano, Hayato,Kutsumura, Noriki,Saito, Takao
, p. 3179 - 3184 (2012/11/14)
A facile synthesis of quinazolin-4(3H)-ones possessing carbon substituents at positions 2 and 3 has been developed. Key to the synthesis is a tandem strategy involving introduction of a 2-substituent and construction of the quinazolinone framework via C-nucleophilic addition to the carbodiimide cumulenic carbon followed by intramolecular nucleophilic substitution by the newly formed NH moiety at the proximal ester group.
Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones
Kshirsagar, Umesh A.,Mhaske, Santosh B.,Argade, Narshinha P.
, p. 3243 - 3246 (2008/02/02)
A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -F
Nafion-H: An efficient and recyclable heterogeneous catalyst for the one-pot synthesis of 2,3-disubstituted 4-(3H)-quinazolinones under solvent-free microwave irradiation conditions
Lingaiah, B. Venkat,Ezikiel,Yakaiah,Reddy, G. Venkat,Shanthan Rao
, p. 2507 - 2509 (2008/02/11)
A one-pot synthesis of 2,3-disubstituted 4-(3H)-quinazolinones has been carried out efficiently by the three-component coupling of isatoic anhydride/anthranilic acid, orthoesters, and amines in the presence of Nafion-H (a perfluorinated resin-supported su
Synthesis and structure-activity relationship of 3-phenyl-3H-quinazolin-4- one derivatives as CXCR3 chemokine receptor antagonists
Storelli, Stefania,Verdijk, Pauline,Verzijl, Dennis,Timmerman, Henk,Van De Stolpe, Andrea C.,Tensen, Cornelis P.,Smit, Martine J.,De Esch, Iwan J. P.,Leurs, Rob
, p. 2910 - 2913 (2007/10/03)
A series of 3-phenyl-3H-quinazolin-4-ones have been synthesized and tested for affinity and activity at the chemokine CXCR3 receptor. The most potent compound (1d) has been evaluated using radioligand binding and calcium mobilization assays and is considered a useful tool for further characterization of the CXCR3 receptor.
Montmorillonite K-10 catalysed solvent-free synthesis of 2,3-disubstituted-4(3H)quinazolinones under microwave irradiation
Dabiri,Salehi,Mohammadi, Ali A.,Baghbanzadeh,Kozehgiry, Gh.
, p. 570 - 572 (2007/10/03)
An efficient and rapid synthesis of 2,3-disubstituted-4(3H)quinazolinones by condensation of 2-aminobenzamide (substituted anthraniamides) with orthoesters in the presence of K-10 clay under solvent free conditions using microwave irradiation or classical heating is described.
