1022-46-4Relevant articles and documents
Pd-carbene catalyzed carbonylation reactions of aryl iodides
Xue, Liqin,Shi, Lijun,Han, Yuan,Xia, Chungu,Huynh, Han Vinh,Li, Fuwei
, p. 7632 - 7638 (2011)
A series of carbene complexes [PdBr2(iPr 2-bimy)L] (C2-C13) with different types of co-ligands (L) have been tested for their catalytic activities in the carbonylative annulation of 2-iodophenol with phenylacetylene in DMF to afford the respective flavone 2a. Complex C12 with an N-phenylimidazole co-ligand showed the best activity and also afforded high yields when the substrate scope was extended to other aryl or pyridyl acetylenes. In addition, catalyst C12 was also efficient in the carbonylative annulation of 2-iodoaniline with acid chlorides giving the desirable 2-substituted 4H-3,1-benzoxazin-4-ones (4) in good yields. Additionally, this Pd-NHC complex also proved to be a very efficient catalyst for the hydroxycarbonylation of iodobenzene derivatives at low catalyst loading and under low CO pressure. These results demonstrate the versatility and efficiency of this phosphine-free Pd(ii)-NHC complex in different types of carbonylations of aryl iodides under mild conditions. The Royal Society of Chemistry 2011.
Reaction of Anthranilic Acid with Orthoesters: A New Facile One-pot Synthesis of 2-Substituted 4H-3,1-Benzoxazin4-ones
Khajavi, Mohammad S.,Montazari, Nasser,Sadat Hosseini
, p. 286 - 287 (1997)
The synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by the condensation of anthranilic acid and orthoesters under classical heating and microwave irradiation is described.
Synthesis of some new benzoxazine derivatives of biological interest
Verma, Manjusha,Singh, Sundaram,Singh
, p. 499 - 502 (2003)
The synthesis of a number of biologically important imino-quinazolones has been achieved by the condensation of 3-amino-2-aryl-4-quinazolone and aromatic aldehydes.
4H-Benzo[d][1,3]oxazin-4-ones and Dihydro analogs from substituted anthranilic acids and orthoesters
Annor-Gyamfi, Joel K.,Bunce, Richard A.
, (2019)
A one-pot route to 2-alkyl and 2-aryl-4H-benzo[d][1,3]oxazin-4-ones (also known as 4H-3,1-benzoxazin-4-ones) has been developed and studied. The method involves the reaction of aryl-substitutedanthranilic acidswithorthoesters inethanol catalyzedby acetic acid. Additionally,wehave also investigated the reaction under microwave conditions. Not all of the substrates were successful in yielding the target heterocycles as some of the reactions failed to undergo the final elimination. This process led to the isolation of (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.
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Cohen,Lipowitz
, p. 4866 (1961)
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Synthesis, characterization, and screening for analgesic and anti-inflammatory activities of new 1,3,4-oxadiazole derivatives linked to quinazolin-4-one ring
Dewangan, Dhansay,Verma, Vinay Sagar,Nakhate, Kartik T.,Tripathi, Dulal Krishna,Kashyap, Pranita,Dhongade, Hemant
, p. 2143 - 2154 (2016)
In the present study, several new 1,3,4-oxadiazole derivatives linked with quinazolin-4-one moiety were synthesized by following steps. 2-methyl -4H-3, 1-benzoxazin-4-one, and 2-phenyl -4H-3, 1-benzoxazin-4-one were synthesized in the first and second step by stirring anthranilic acid in pyridine with benzoyl chloride and with an acetic anhydride for 30 min at room temperature. On treatment with semicarbazide with the above synthesized intermediates, that is, 2-methyl-4H-3,1-benzoxazin-4-one, and 2-phenyl-4H-3,1-benzoxazin-4-one in the third step afforded 2-methyl-4-oxoquinazoline-3(4H)-carbohydrazide and 2-phenyl-4-oxoquinazoline-3(4H)-carbohydrazide. These were introduced in cyclization reaction with different aromatic acids, aromatic aldehydes, and carbon disulfide in the next step, producing the corresponding 3-(4-acetyl-5-aryl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2-phenyl-quinazolin-4(3H)-one derivatives, 3-(4-acetyl-5-aryl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2-methyl-quinazolin-4(3H)-one derivatives, 3-(5-aryl-1,3,4-oxadiazol-2-yl)-2-phenylquinazolin-4(3H)-one derivatives and 3-(5-aryl-1,3,4-oxadiazol-2-yl)-2-methylquinazolin-4(3H)-one derivatives. Purity of these synthesized derivatives was confirmed by thin layer chromatography, melting point. Structure of the derivatives was set up by determining infrared spectroscopy, nuclear magnetic resonance, and mass spectroscopy. All the synthesized derivatives were evaluated for their analgesic and anti-inflammatory activities in mice and rats. In animal studies, the derivatives 3-[4-acetyl-5-(2-hydroxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-phenylquinazolin-4(3H)-one and 3-[4-acetyl-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-phenylquinazolin-4(3H)-one shown more potent analgesic activity and the derivatives 3-[4-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-phenylquinazolin-4(3H)-one and 3-[4-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-methylquinazolin-4(3H)-one shown more potent anti-inflammatory activity as compared to other derivatives. The results of current study indicate that cyclization of carbohydrazide group of intermediate 2-methyl-4-oxoquinazoline-3(4H)-carbohydrazide and 2-phenyl-4-oxoquinazoline-3(4H)-carbohydrazide with different aromatic acids, aromatic aldehydes, and carbon disulfide produces novel quinazolin-4-one linked oxadiazole derivatives with potent analgesic and anti-inflammatory activities.
Palladium (0)-catalyzed C(sp2)-H oxygenation with carboxylic acids
Gong, Ai-Jun,Li, Xu-Qin,Vu, Huu-Manh,Yong, Jia-Yuan
, (2020)
Palladium (0)-catalyzed Ortho-benzoxylation of the sp2 C–H bond of arylbenzoxazinones with carboxylic acid is reported. With benzoxazinone as directing group, the reaction went smoothly under the benign condition and gave the desired product wi
Design, synthesis and assessment of new series of quinazolinone derivatives as EGFR inhibitors along with their cytotoxic evaluation against MCF7 and A549 cancer cell lines
Aziz, Marian W.,Kamal, Aliaa M.,Mohamed, Khaled O.,Elgendy, Adel A.
, (2021)
New acetamide (IV a-e) and 1,3-thiazolidinone derivatives (VII a-e) were designed, synthesized and assessed for their cytotoxic activity against MCF-7 and A549 cell lines along with their lead compounds (erlotinib and gefitinib). The newly designed compou
Synthesis, characterization and antimicrobial activity of new 2-phenylquinoline-4(3H)-one derivatives
Samir, Ali Hammadi
, p. 1422 - 1432 (2017)
Quinazolinones is an important chemical synthesis with different physiological significance and pharmacological utility. Reaction of anthranilic acid with benzoyl chloride in pyridine yielded 2-phenyl-4H-benzo[d][1,3]oxazin-4-one, which on condensation reaction with the tryptophan in glacial acetic acid afforded 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanoic acid (2). Treatment of compound (2) with thionyl chloride produced 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanoyl chloride (3).Condensation of compound (3) with hydrazine hydrate gave 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanehydrazide (4). Condensation of compound (4) with ethyl aceto acetate in glacial acetic acid yielded 3-(3-(1H-indol-3-yl)-1-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)-1-oxopropan-2-yl)-2-phenylquinazolin-4(3H)-one (5). The reaction of compound (4) with carbon disulfide and sodium hydroxide yielded3-(2-(1H-indol-3-yl)-1-(5-mercapto-1,3,4-oxadiazol-2-yl) ethyl)-2-phenylquinazolin-4(3H)-one (6).Condensation of compound (6) with hydrazine hydrate afforded 2-hydrazinyl-5- (2-(1H-indol-3-yl) ethyl)-2-phenylquinazolin-4(3H)-one(7). Compound (8) 2-(3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl)propanoyl)-2,3-dihydrophthalazine-1,4-dione was synthesized by condensing compound (4) with phthalic anhydride in glacial acetic acid. When compound (4) was reacted with different aromatic aldehydes in abs. ethanol afforded different substituted (9a-d).Moreover, N-(1,5-dioxo-3-substituted-1,5-dihydrobenzo[e][1,3] oxazepin-4(3H)-yl)-3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanamide (10a,b) were prepared from the cyclic condensation of Schiff bases compounds with phthalic anhydride. The structures of newly synthesized compounds were characterized by m.p., TLC, FTIR and 1H, 13C-NMR spectral analysis. The antimicrobial activity of the synthesized phenylquinazoline on two kinds of bacteria namely, staphylococcus aureous and Escherichia coli was investigated.
A general palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones from 2-bromoanilines and acid anhydrides
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
, p. 12599 - 12602 (2012)
(C), its (O)K! An efficient palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones has been developed (see scheme). By starting from 2-bromoanilines and acid anhydrides, the corresponding products were isolated in good yields. Copyright
Silver and Palladium Cocatalyzed Carbonylative Activation of Benzotriazoles to Benzoxazinones under Neutral Conditions
Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
, p. 6232 - 6235 (2017)
A novel and efficient method for the carbonylative activation of benzotriazoles to benzoxazinones has been developed. By using a silver and palladium bimetallic catalyst system, a broad range of benzotriazoles were transformed into the corresponding benzoxazinones in moderate to good yields with excellent functional group tolerance. Notably, this procedure proceeds under neutral conditions.
RETRACTED ARTICLE: Palladium-Catalyzed Decarboxylative Selective Acylation of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with α-Oxo Carboxylic acids via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
Majhi, Biju,Kundu, Debasish,Ghosh, Tubai,Ranu, Brindaban C.
, p. 283 - 295 (2016)
The benzoxazine scaffolds are of much interest as they are found in a large array of natural products and pharmaceutical drugs with diverse activities. We have developed a palladium-catalyzed decarboxylative selective mono- and bis-acylation of 4H-benzo[d
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Eckroth,Squire
, p. 312 (1969)
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Pinkus et al.
, p. 242 (1970)
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Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones
Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Mahmood, Nasir,Yar, Muhammad,Zahoor, Ameer Fawad
, p. 152 - 156 (2013)
Twenty derivatives of 2-aryl-4H-3,1-benzoxazin-4-one synthesized and their potential therapeutically significance tested against two strains of Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and four strains of Gram negative bacteria (Shigella flexnari, Escherichia coli, Salmonella typhi and Pseudomonas aeruginsoa) by agar well diffusion method. The 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one (3f) recorded significant antibacterial activity against Bacillus subtilis whereas 2-(4-bromophenyl)-4H-3, 1-benzoxazin-one (3o) exhibited weak antibacterial activity against Staphylococcus aureus. Further 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one (3b) showed significant activity against Shigella Flexnari, Escherichia coli, Pseudomonas aeruginsoa and Salmonella typhi. The antibacterial activity of synthesized derivatives of 2-aryl-4H-3,1-benzoxazin-4-one was compared to reference standard antibiotics amoxycillin, streptomycin, kanamycin and ciprofloxacin. The present study revealed that 2-aryl-4H-3,1-benzoxazin-4-ones possess good bactericidal activity against a panel of bacteria causing common bacterial diseases and therefore opens the possibility of finding latest clinically useful antibacterial compounds. The synthesized compounds were characterized by 1H NMR, EI, FT-IR and elemental analysis.
Silver- versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone
Arcadi,Chiarini,Vecchio, L. Del,Marinelli,Michelet
, p. 1458 - 1461 (2016)
Unprecedented domino oxidative cyclization reactions of unprotected 2-alkynylanilines to give functionalized 4H-benzo[d][1,3]oxazin-4-one or benzisoxazole derivatives in moderate to good yields are achieved by silver vs. gold selective catalysis. The search for the optimal reaction conditions revealed the divergent catalytic activity of NaAuCl4·H2O and AgNO3.
A synthetic approach and molecular docking study of hybrids of quinazolin-4-ones and thiazolidin-4-ones as anticancer agents
Thakral, Samridhi,Saini, Deepika,Kumar, Ashwani,Jain, Neelam,Jain, Sandeep
, p. 1595 - 1604 (2017)
A series of 3-(4-(2-(aryl)-4-oxothiazolidin-3-yl)phenyl-2-phenylquinazolin-4(3H)-one derivatives were synthesized in appreciable yield by using anthranilic acid as a starting material. The structures of synthesized compounds (QT1–QT10) were confirmed on t
Copper-mediated oxidative tandem reactions with molecular oxygen: Synthesis of 2-arylbenzoxazinone derivatives from indoles
Yamashita, Mitsuaki,Iida, Akira
, p. 2991 - 2993 (2014)
We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl an
Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents
Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro
supporting information, p. 3245 - 3249 (2021/06/08)
The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger-scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability. (Figure presented.).
Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
Yu, Yongqi,Xia, Zhen,Wu, Qianlong,Liu, Da,Yu, Lin,Xiao, Yuanjiu,Tan, Ze,Deng, Wei,Zhu, Gangguo
, p. 1263 - 1266 (2020/10/08)
A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.
