25855-20-3Relevant academic research and scientific papers
2-Chloroquinazoline. Synthesis and reactivity of a versatile heterocyclic building block
Henriksen, Signe Teuber,S?rensen, Ulrik Svane
, p. 8251 - 8254 (2006)
Starting from 2,4-dichloroquinazoline, various methods for the selective removal of the 4-chloro substituent were tested, including catalytic hydrogenation, metal-halogen exchange, metal hydride reduction and reduction with tributyltin hydride-the latter
Method for catalyzing nitrogen heterocyclic ring aerobic dehydrogenation based on ionic liquid porous carbon material
-
Paragraph 0057-0060, (2022/01/24)
The invention discloses a method for catalyzing nitrogen heterocycle aerobic dehydrogenation based on an ionic liquid porous carbon material, and is suitable for the field of organic synthesis. A heterogeneous catalysis system takes nitrogen heterocycle and derivatives thereof as substrates, a carbon material as a catalyst, water or ethanol as a solvent and air or oxygen spheres as an oxygen source, and a reaction is carried out at 0-80 DEG C under normal pressure, oxidative dehydrogenation of nitrogen heterocyclic compounds can be realized, and target products such as indole, quinoline, isoquinoline, quinazoline, quinoxaline, benzothiazole, Hanus ester and derivatives thereof and other medical intermediates can be synthesized. The non-metal catalyst is prepared by using the ionic liquid as the precursor, no activating agent or other additives are used in the reaction process, and the method has industrial application prospects.
BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions
Luo, Lan,Liu, Hongqiang,Zeng, Wei,Hu, Wenkang,Wang, Dawei
, (2021/11/16)
Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.
Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides
Zhang, Shi-Qi,Cui, Yao,Guo, Bin,Young, David J.,Xu, Ze,Li, Hong-Xi
, (2020/12/13)
The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.
Efficient access to quinolines and quinazolines by ruthenium complexes catalyzed acceptorless dehydrogenative coupling of 2-aminoarylmethanols with ketones and nitriles
Feng, Qi,Han, Zhangang,Hao, Zhiqiang,Huo, Shuaicong,Kong, Siqi,Lin, Jin,Lu, Guo-Liang,Zeng, Guang
, (2021/09/08)
Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands, 2-(CR1R2OH)-6-[3,5-(R3)2C3HN2]C5H3N (R1 = R2 = Me, R3 = H (L1H); R1 = Me, R2 = Ph, R3 = H (L2H); R1 = R2 = Ph, R3 = H (L3H); R1 = R2 = R3 = Me (L4H)) with RuCl3?xH2O in refluxing EtOH afforded the corresponding Ru(III) complexes L2RuCl (1a-1d), which were well characterized by IR, HR-MS and X-ray single crystal structural determination. These Ru complexes showed similarly high catalytic performance for both dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, giving the quinolines and quinazolines in good to excellent yields. This protocol provides an atom-economical and sustainable route to access various structurally important quinoline and quinazoline derivatives by using phosphine-free ligand based Ru catalysts.
Mn(iii)-mediated cascade cyclization of 1-(azidomethyl)-2-isocyanoarenes with organoboronic acids: Construction of quinazoline derivatives
Kumar, Gujjenahalli Ramalingaiah Yogesh,Begum, Noor Shahina
, p. 9811 - 9817 (2021/06/15)
A novel and efficient Mn(iii)-mediated oxidative radical cascade reaction of 1-(azidomethyl)-2-isocyanoarenes with organoboronic acids is reported. The single electron oxidation of a commercially available organo boronic acid in the presence of a mild oxidant, Mn(OAc)3·2H2O, resulted in moderate yields of the corresponding quinazoline derivatives.
K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
Hunjan, Mandeep Kaur,Laha, Joydev K.
supporting information, p. 8437 - 8440 (2021/09/02)
While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.
Palladium-catalyzed carbonylative synthesis of quinazolines: Silane act as better nucleophile than amidine
Lu, Jia-Ming,Huo, Yong-Wang,Qi, Xinxin,Wu, Xiao-Feng
, (2021/05/31)
A palladium-catalyzed reductive carbonylation reaction has been developed for the synthesis of quinazolines. With N-(2-iodophenyl)benzimidamide as starting materials, a series of quinazolines were obtained through the aromatic aldehyde intermediates in moderate to good yields with good functional group compatibilities. In this system, silane act as better nucleophile than amidine.
Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes
Zhang, Xiangyu,Luo, Chujun,Chen, Xiaoyong,Ma, Weilin,Li, Bin,Lin, Zirui,Chen, Xiuwen,Li, Yibiao,Xie, Feng
, (2021/02/20)
A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.
Mixed crystalline phases and catalytic performance of OMS-2 based nanocomposites for one-pot synthesis of quinazolines with O2 as an oxidant
Yao, Nan,Bi, Xiuru,Zhang, Liping,Tao, Luyao,Zhao, Peiqing,Meng, Xu,Liu, Xiang
, (2021/03/03)
In this work, a series of sodium phosphotungstate modified manganese oxide octahedral molecular sieve (OMS-2) catalysts ([PW]-OMS-2) were developed, and their catalytic activities were investigated by one-pot synthesis of quinazolines from benzyl alcohol and 2-aminobenzylamine with O2 as green oxidant in dimethyl carbonate (DMC). TEM, XRD and EDS confirmed that sodium phosphotungstate decomposed into phosphotungstic acid and sodium tungstate in the doping process. Meanwhile, phosphotungstic acid attached and located at the surface of OMS-2 and W ions were successfully doped into the OMS-2 framework. For comparison, phosphotungstic acid/OMS-2 was prepared by simple wet impregnation method. The [PW]-OMS-2 is the most highly selective and effective over than phosphotungstic acid/OMS-2 and OMS-2 itself in the one-pot synthesis of quinazolines. It may be due to the synergetic effect of phosphotungstic acid and OMS-2, and successfully doping W into OMS-2 frameworks. Hence, this work provides a new environmentally-friendly and heterogeneous OMS-2 based nanocomposites and it may be put into practice to synthesize heterocyclic compounds.
