24122-33-6Relevant articles and documents
Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones
Govindan, Karthick,Duraisamy, Tamilselvan,Jayaram, Alageswaran,Senadi, Gopal Chandru,Lin, Wei-Yu
supporting information, p. 1115 - 1124 (2021/12/02)
A simple copper-catalyzed assembly to formulate quinazolinone and indazolone derivatives in a single protocol manner is reported. These transformations are based on the fact that DMF can serve as a reaction solvent and one carbon synthon for the construct
New and efficient synthesis of 3-arylquinazolin-4(1H)-ones and biologically important N-fused tetracycles based on N-(2-carboxyphenyl)oxalamide
Mamedov, Vakhid A.,Mamedova, Vera L.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Voronina, Julia K.,Kushatov, Temur A.,Korshin, Dmitry E.,Samigullina, Aida I.,Tanysheva, Ekaterina G.,Kh. Rizvanov, Il'dar,Latypov, Shamil K.
, (2021/09/28)
A novel clean, one-pot syntheses of 3-arylquinazolin-4(3H)-ones and quinoxalino[2,1-b]quinazoline-6,12(5H)-diones via PPA-mediated coupling of N-(2-carboxyphenyl)oxalamides with arylamines and 1,2-benzenediamines have been developed. Under mild reaction conditions with use of Na2S2O4 the benzimidazo[2,1-b]quinazolin-12-ones were achieved in good yield from 3-(2-nitrophenyl)quinazolin-4-ones.
Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides
Chen, Fen-Er,Dong, Lin,Li, Hongyan,Liu, Jinxin,Luo, Liangliang,Xiao, You-Cai,Zhou, Yuan
, p. 29257 - 29262 (2020/10/02)
A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is
Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
supporting information, p. 5726 - 5733 (2020/08/21)
N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.
New Strategy for the Synthesis of Heterocycles via Copper-Catalyzed Oxidative Decarboxylative Amination of Glyoxylic Acid
Niu, Bin,Li, Shaoqing,Cui, Chang,Yan, Yizhe,Tang, Lin,Wang, Jianyong
supporting information, p. 7800 - 7803 (2019/11/28)
A copper-catalyzed oxidative decarboxylative amination of glyoxylic acid with substrates having two nitrogen-nucleophilic sites was first demonstrated. Using this novel approach, 1,3,5-triazines, quinazolinones and quinazolines were obtained in up to 93 % yields. Notably, glyoxylic acid was employed as the C1 synthon for heterocycles. This strategy enriches the application of glyoxylic acid for the synthesis of valuable heterocycles.
Transition metal-free C-F/C-Cl/C-C cleavage of ClCF2COONa for the synthesis of heterocycles
Yan, Yizhe,Cui, Chang,Wang, Jianyong,Li, Shaoqing,Tang, Lin,Liu, Yanqi
supporting information, p. 8071 - 8074 (2019/09/19)
A transition metal-free and external oxidant-free annulation of substrates having two nitrogen-nucleophilic sites with ClCF2COONa was demonstrated, affording a series of 1,3,5-triazines and quinazolinones in up to 96% yields. Notably, ClCF
Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon
Lee, Seohoo,Sim, Jaeuk,Jo, Hyeju,Viji, Mayavan,Srinu, Lanka,Lee, Kiho,Lee, Heesoon,Manjunatha, Vishwanath,Jung, Jae-Kyung
supporting information, p. 8067 - 8070 (2019/09/19)
Biologically important quinazolinones have been synthesized from 2-aminobenzamides and DMSO. The key feature of the reaction is the utilization of DMSO as a methine source for intramolecular oxidative annulation. The CNS depressant drug methaqualone has also been synthesized by our methodology. The present method involves the synthesis of quinazolinones with a broad substrate scope and a good yield.
Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
supporting information, p. 979 - 985 (2019/03/12)
Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
A Domino Process for the Sustainable Synthesis of Quinazolin-4(3 H)-ones with Direct Chemo- and Regioselective Bromination
Sheikhi, Ehsan,Adib, Mehdi,Yazzaf, Rozita,Jahani, Mehdi,Ghavidel, Mehdi
supporting information, p. 2046 - 2050 (2018/09/18)
An efficient approach is reported for the direct and sustainable construction of quinazolin-4(3 H)-ones through a three-component reaction of isatoic anhydride, primary amines, and bromoacetyl bromide or chloroacetyl chloride in the presence of K 2 CO 3 in DMSO. With bromoacetyl bromide, mono- or dibrominated quinazolinone scaffolds were obtainable in a chemo- and regioselective manner.
TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3H)-ones and Quinazolines by Oxidative Amination of C(sp3)–H Bond
Mukhopadhyay, Sushobhan,Barak, Dinesh S.,Batra, Sanjay
, p. 2784 - 2794 (2018/06/04)
tert-Butyl hydroperoxide (TBHP) served as the methyl source under metal-free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin-4(3H)-ones and quinazolines from 2-aminobenzamides and 2-carbonyl-substituted anilines, respectively.
