Eco-friendly, green and new metal-free intramolecular Friedel-Crafts reaction to synthesis of Acridones derivatives using phenylboronic acid derivatives

被引:2
作者
Askarzadeh, Mohammad [1 ]
Moazzam, Ali [2 ]
Sayahi, Mohammad Hosein [3 ]
Fouladvand, Aida [2 ]
Adib, Mehdi [1 ]
Mahdavi, Mohammad [2 ]
机构
[1] Univ Tehran, Coll Sci, Sch Chem, Tehran, Iran
[2] Univ Tehran Med Sci, Endocrinol & Metab Clin Sci Inst, Endocrinol & Metab Res Ctr, Tehran, Iran
[3] Payame Noor Univ PNU, Dept Chem, Tehran, Iran
关键词
Acridones; Metal -free intramolecular C -C bond; formation; Carbonylation; Friedel-Crafts reaction; C-H ACTIVATION; CYCLIZATION; LIMITATIONS;
D O I
10.1016/j.tetlet.2023.154532
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a new, facile, versatile metal-free method for preparation of the various Acridones through an intramolecular carbonylation of 2-(phenylamino)benzoic acid derivatives and phenylboronic acid derivatives as activating agent for activation of carboxylic acid group in intramolecular C-C bond formation through Friedel-Crafts reaction. The reaction proceeds under solvent-free conditions, tolerates a wide range of functional groups, and provides rapid access to a range of the Acridones in good to excellent yields.
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页数:5
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共 34 条
[1]  
[Anonymous], 1939, ORG SYNTH, V19, P6
[2]   Design, synthesis, and biological properties of new bis(acridine-4-carboxamides) as anticancer agents [J].
Antonini, I ;
Polucci, P ;
Magnano, A ;
Gatto, B ;
Palumbo, M ;
Menta, E ;
Pescalli, N ;
Martelli, S .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :3109-3115
[3]   A efficient, metal-free and sustainable synthesis, C-S linked by simple C-H thiocyanation of 4-aminocoumarin or 4-(N-aryl)aminocoumarin derivativess [J].
Askarzadeh, Mohammad ;
Moazzam, Ali ;
Vojdanitalab, Khashayar ;
Hosseini, Samanesadat ;
Adib, Mehdi ;
Mahdavi, Mohammad .
TETRAHEDRON, 2023, 134
[4]   Recent advances in the transition-metal-free synthesis of quinoxalines [J].
Borah, Biplob ;
Chowhan, L. Raju .
RSC ADVANCES, 2021, 11 (59) :37325-37353
[5]   C-H Activation: Toward Sustainability and Applications [J].
Dalton, Toryn ;
Faber, Teresa ;
Glorius, Frank .
ACS CENTRAL SCIENCE, 2021, 7 (02) :245-261
[6]   Discovery and Structural Optimization of Acridones as Broad-Spectrum Antimalarials [J].
Dodean, Rozalia A. ;
Kancharla, Papireddy ;
Li, Yuexin ;
Melendez, Victor ;
Read, Lisa ;
Bane, Charles E. ;
Vesely, Brian ;
Kreishman-Deitrick, Mara ;
Black, Chad ;
Li, Qigui ;
Sciotti, Richard J. ;
Olmeda, Raul ;
Thu-Lan Luong ;
Gaona, Heather ;
Potter, Brittney ;
Sousa, Jason ;
Marcsisin, Sean ;
Caridha, Diana ;
Xie, Lisa ;
Vuong, Chau ;
Zeng, Qiang ;
Zhang, Jing ;
Zhang, Ping ;
Lin, Hsiuling ;
Butler, Kirk ;
Roncal, Norma ;
Gaynor-Ohnstad, Lacy ;
Leed, Susan E. ;
Nolan, Christina ;
Huezo, Stephanie J. ;
Rasmussen, Stephanie A. ;
Stephens, Melissa T. ;
Tan, John C. ;
Cooper, Roland A. ;
Smilkstein, Martin J. ;
Pou, Sovitj ;
Winter, Rolf W. ;
Riscoe, Michael K. ;
Kelly, Jane X. .
JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (07) :3475-3502
[7]   Copper Catalyst-Supported Modified Magnetic Chitosan for the Synthesis of Novel 2-Arylthio-2,3-dihydroquinazolin-4(1H)-one Derivatives via Chan-Lam Coupling [J].
Ghasemi, Nastaran ;
Yavari, Ali ;
Bahadorikhalili, Saeed ;
Moazzam, Ali ;
Hosseini, Samanehsadat ;
Larijani, Bagher ;
Iraji, Aida ;
Moradi, Shahram ;
Mahdavi, Mohammad .
INORGANICS, 2022, 10 (12)
[8]   N-Arylation Reaction of 2-Amino-N-phenylbenzamide with Phenyl Boronic Acid via Chan-Evans-Lam (CEL) Type Reaction Using Cu@Phen@MGO Catalyst [J].
Ghasemi, Nastaran ;
Moazzam, Ali ;
Bahadorikhalili, Saeed ;
Yavari, Ali ;
Hosseini, Samanehsadat ;
Sayahi, Mohammad Hossein ;
Larijani, Bagher ;
Hamedifar, Haleh ;
Ansari, Samira ;
Mahdavi, Mohammad .
CATALYSIS LETTERS, 2023, 153 (03) :805-813
[9]   FRIEDEL-CRAFTS ACYLATION OF ALKENES [J].
GROVES, JK .
CHEMICAL SOCIETY REVIEWS, 1972, 1 (01) :73-&
[10]   Boronic acid catalysis [J].
Hall, Dennis G. .
CHEMICAL SOCIETY REVIEWS, 2019, 48 (13) :3475-3496