5363-37-1Relevant articles and documents
Iron-Catalyzed Oxidative Amination of Benzylic C(sp3)–H Bonds with Anilines
Song, Yan-Ling,Li, Bei,Xie, Zhen-Biao,Wang, Dan,Sun, Hong-Mei
, p. 17975 - 17985 (2021/12/13)
Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr4] showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr4] was more efficient for EDG-substituted anilines. This work provides alternative access to benzylamines with the advantages of both a wide substrate scope and iron catalysis.
Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
supporting information, p. 5435 - 5441 (2020/08/03)
Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
Rotondi, Giulia,Guglielmi, Paolo,Carradori, Simone,Secci, Daniela,De Monte, Celeste,De Filippis, Barbara,Maccallini, Cristina,Amoroso, Rosa,Cirilli, Roberto,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
, p. 1400 - 1413 (2019/08/26)
A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.
Mechanistic insights into a catalyst-free method to construct quinazolinones through multiple oxidative cyclization
Wang, Zhen-Zhen,Tang, Yu
, p. 1330 - 1336 (2017/02/15)
A novel one-pot benign oxidative cyclization of alcohols with 2-aminobenzamides was successfully developed without catalyst to afford the quinazolinones under O2. This one-pot protocol involved oxidations and cyclizations to construct the skeleton of quinazolinones through possibly three kinds of distinct reaction mechanisms.
One-Pot Copper(I)-Catalyzed Ligand/Base-Free Tandem Cyclooxidative Synthesis of Quinazolinones
Upadhyaya, Kapil,Thakur, Ravi Kumar,Shukla, Sanjeev K.,Tripathi, Rama Pati
, p. 5046 - 5055 (2016/07/06)
A novel and efficient Cu(I)-catalyzed ligand- and base-free multipathway domino strategy has been developed for the synthesis of 2-substituted quinazolinones. The reaction utilizes 2-bromobenzamide and multiform substrates such as aldehydes, alcohols, and methyl arenes for a one-pot protocol, whereas TMSN3 is used as a nitrogen source. A wide range of substrate scope, functional group tolerance, and operational simplicity are synthetically useful features.
Sulfate Radical Anion (SO4?-) Mediated C(sp3)-H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles
Laha, Joydev K.,Tummalapalli, K. S. Satyanarayana,Nair, Akshay,Patel, Nidhi
, p. 11351 - 11359 (2015/12/01)
A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C(sp3)-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.
Naryl-substituted anthranilamides with intramolecular hydrogen bonds
Wang, Li-Xia,Hu, Ben-Quan,Xiang, Jun-Feng,Cui, Jie,Hao, Xiang,Liang, Tong-Ling,Tang, Ya-Lin
supporting information, p. 8588 - 8591 (2014/12/11)
Hydrogen bonding interaction as one type of non-covalent force has proven itself to be highly efficient for constructing structurally unique artificial secondary structures. Here, the structure of Naryl-substituted anthranilamide in solution is demonstrated by various NMR technique, the intramolecular hydrogen bonds between amide attached to arylamine of the same ring is proposed, which is supported by its crystal structure in the solid phase. The substituent on the nitrogen atom of arylamine plays an important role in forming the presence of intramolecular hydrogen bonds. The chemical shift of the Naryl-H downfield changes obviously, due to the formation of intramolecular hydrogen bonds and the deshielding effect of oxygen, and the neighboring C-H is activated and shows downfield protonic signal too. The presence of intramolecular hydrogen bonds probably provides the explanation for the transformation from Naryl-substituted anthranilamide to imine, which could be converted into 2-aryl quinazolinone finally.
Efficient construction of C=N double bonds via acceptorless dehydrogenative coupling
Sun, Xiang,Hu, Yu,Nie, Shao-Zhen,Yan, Yun-Yun,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 2179 - 2184 (2013/10/01)
The efficient construction of C=N double bonds has been achieved by the Ir-catalyzed intramolecular acceptorless dehydrogenative cross-coupling of tertiary amines and amides. An iridium/2-hydroxypyridine complex was identified as the highly efficient catalyst. A number of quinazolinone derivatives was prepared in excellent yields. An iridium-mediated C-H activation mechanism is proposed. This finding provides an unprecedented strategy for the direct imidation of sp3 C-H bonds.
Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: A strategy to construct quinazolinones
Hikawa, Hidemasa,Ino, Yukari,Suzuki, Hideharu,Yokoyama, Yuusaku
experimental part, p. 7046 - 7051 (2012/10/07)
A novel method for the synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C-H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.
Copper-catalyzed domino synthesis of quinazolinones via Ullmann-type coupling and aerobic oxidative C-H amidation
Xu, Wei,Jin, Yibao,Liu, Hongxia,Jiang, Yuyang,Fu, And Hua
supporting information; experimental part, p. 1274 - 1277 (2011/04/24)
An efficient copper-catalyzed approach to quinazolinone derivatives has been developed, and the protocol uses cheap and readily available substituted 2-halobenzamides and (aryl)methanamines as the starting materials as well as economical and environmentally friendly air as the oxidant. This can be the first example of constructing N-heterocycles via sequential Ullmann-type coupling under air and aerobic oxidative C-H amidation.
