Oxazinone Derivatives Research Articles

B(C6F5)3-catalyzed Wolff rearrangement/[2 + 2] and [4 + 2] cascade cyclization of α-diazoketones with imines

B(C6F5)3-catalyzed [2 + 2] cyclizations of α-diazoketones withN-tert-butoxycarbonyl imines affords 20 β-lactams in up to 94% yield, while reactions of α-diazoketones withN-benzoyl imines gave 14 oxazinone derivatives in up to 95% yield.

Application of 1,4-Oxazinone Precursors to the Construction of Pyridine Derivatives by Tandem Intermolecular Cycloaddition/Cycloreversion.

This study reveals a new method for the preparation of 1,4-oxazinone derivatives by Staudinger reductive cyclization of functionalized vinyl azide precursors. The resulting oxazinone derivatives prepared in this manner were intercepted with terminal alkyne substrates through an intermolecular cycloaddition/cycloreversion sequence to afford polysubstituted pyridine products. Alkyne substrates bearing propargyl oxygen substitution showed good regioselectivity in the cycloaddition operation selectively affording 2,4,6-substituted pyridines. Application of this chemistry to the synthesis of an ErbB4 receptor inhibitor is also described.

Quantum Chemical Calculations and Statistical Analysis: Structural Cytotoxicity Relationships of some Synthesized 2-thiophen-naphtho(benzo)oxazinone Derivatives.

Twenty-two 2-thiophen-naphtho(benzo)oxazinone derivatives are prepared using 3-amino-2-naphthoic and 5-nitroanthranilic acids as building blocks. The target compounds (1-22) were evaluated quantitatively for their cytotoxic effects in vitro against three cancer cell lines, including the lung A549, the hepatocyte HepG2, and the breast MCF-7 carcinoma cells. Compounds 1, 12, 14, and 21 were found to exhibit remarkable cytotoxicity against the tested cancer cell lines. Compound 21 has shown the highest activity against A549 and MCF-7 (IC50: 9.8 & 3.6 µg mL-1) whereas 1 (IC50: 5.9 µg mL-1) and 5 (3.6 µg mL-1) were the most active against HepG2. To elucidate the structure-cytotoxicity relationships of the synthesized compounds, a number of their chemical descriptors are determined including electronic, steric and hydrophobicity descriptors. The electronic properties were calculated through density functional theory (DFT) calculations at the B3LYP/6-31 + G(d,p). The impact of the chosen descriptors is evaluated statistically through simple and multiple linear regression analyses (SLR and MLR). SLR analyses reveal that the impact of each descriptor on the cell lines are relatively weak except for MCF-7, where hardness and softness show moderate correlations with correlation coefficients higher than 60%. The correlations were improved by considering MLR analyses (R2 ≥ 90%), which showed that the cytotoxicity of synthesized compounds is correlated with their combined descriptors hardness, softness, electrophiliciy and hydrophobicity (LogP).

Reactions of Huisgen Zwitterions with Diphenyl Cyclopropenone: A Novel Strategy for the Synthesis of Oxazinone Derivatives

Reactions of Huisgen Zwitterions with Diphenyl Cyclopropenone: A Novel Strategy for the Synthesis of Oxazinone Derivatives

ACCESS TO CONVENIENT SYNTHESIS OF OXAZINONE AND PYRIMIDINONE HETEROCYCLES DERIVED FROM 2(3H)-FURANONE

The conversion of the 2(3 H )-furanone into the oxazinone and pyrimidinone derivatives is studied. A 2-(furan-3-ylmethylene)-4-oxo-4-phenylbutanoyl azide 3 was synthesized to carry out these conversions through its thermolysis in dry benzene and/or base-catalyzed decomposition of this azide in the presence of different amines. The structures of all compounds were demonstrated from their spectral data and elemental analyses.

Mini review on synthesis, antimicrobial and cytotoxic activities of oxazinone derivatives

There has been considerable interest in the development of novel oxazinone compounds with as anti-inflammatory, antimicrobial and anti-HIV, anticancer activities. Oxazinones are possessing important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. These observations have been guiding for the development of new oxazinones that possess varied biological activities.

Research on Biological Materials with Oxazinone Derivatives Induce Apoptosis in HT-29 Cells

Objective: To monitor the induction of apoptosis in HT-29 cells by three compounds of oxazinone derivatives (A-C) with similar structures and research the mechanism of those oxazinone derivatives in induction of apoptosis in HT-29 cells. Methods: HT-29 cells were used for the determination of cytotoxicity elicited by oxazinone compounds. Cytotoxic effects of these compounds in HT-29 cells are monitored by a Real-Time Cell Analyser system. Results: All the oxazinone derivatives exhibited growth inhibition in HT-29 cells in a concentration-dependent manner. Conclusion: All the three compounds of oxazinone derivatives (A-C) could exhibit growth inhibition in HT-29 cells in a dose-dependent manner.

Synthesis of pyrido[2,1-a]isoquinolin-4-ones and oxazino[2,3-a]isoquinolin-4-ones: New inhibitors of mitochondrial respiratory chain

Benzo[a]quinolizine is an important heterocyclic framework that can be found in numerous bioactive compounds. The general scheme for the synthesis of these compounds was based on the preparation of the appropriate dihydroisoquinolines by Bischler–Napieralski cyclization with good yields, followed by the Pemberton method to form the oxazinones or pyridones derivatives via acyl-ketene imine cyclocondensation. All the synthesized compounds were assayed in vitro for their ability to inhibit mitochondrial respiratory chain. Most of the tested compounds were able to inhibit the integrated electron transfer chain, measured as NADH oxidation, which includes complexes I, III and IV, in the low micromolar range. Oxazino[2,3-a]isoquinolin-4-ones displayed greater activity than their pyrido[2,1-a]isoquinolin-4-ones analogs. Indeed, the presence of a furan ring in C2 position of oxazino[2,3-a]isoquinolin-4-ones provided the compound (1g) with the most potent biological activity. Therefore, these compounds and especially the oxazinone derivatives are in the tendency of the new less toxic antitumor agents that target mitochondrial electron transport chain in a middle range potency.

Bi-SO3H-functionalized room temperature ionic liquids based on bipyridinium: highly efficient and recyclable catalysts for the synthesis of naphthalene-condensed oxazinone derivatives

Download options Please wait... Article information DOI https://doi.org/10.1039/C3RA00133D Article type Paper Submitted 09 Jan 2013 Accepted 10 Apr 2013 First published 10 Apr 2013 Download Citation RSC Adv., 2013,3, 9965-9972 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS Permissions Request permissions Bi-SO3H-functionalized room temperature ionic liquids based on bipyridinium: highly efficient and recyclable catalysts for the synthesis of naphthalene-condensed oxazinone derivatives Y. Wang, J. Zhou, K. Liu and L. Dai, RSC Adv., 2013, 3, 9965 DOI: 10.1039/C3RA00133D To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page. If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given. If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page. Read more about how to correctly acknowledge RSC content. Social activity Tweet Share Search articles by author Yuanyuan Wang Junlong Zhou Kun Liu Liyi Dai

Synthesis and Antimicrobial Activity of Some New Pyrimidinone and Oxazinone Derivatives Fused with Thiophene Rings Using 2-Chloro-6-ethoxy-4-acetylpyridine as Starting Material

A series of pyridines, pyrimidinones, oxazinones and their derivatives were synthesized as antimicrobial agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. α,β-Unsaturated ketones 3a–c were condensed with cyanothio-acetamide in the presence of ammonium acetate to give 2-cyanopyridinethiones 4a–c, which were reacted with ethyl chloroacetate to yield the corresponding cyano esters 5a–c. The esters 5a–c were cyclized by action of sodium methoxide to aminoesters 6a–c, which were aminolyzed with ammonia to corresponding aminoamide derivatives 7a-c. Also, the esters 6a–c were hydrolyzed with NaOH to the corresponding sodium salt 8a–c, which were treated with acetic anhydride to afford 2-methyloxazinones 9a–c. The latter compounds were treated with ammonium acetate to afford 2-methylpyrimidinones 10a–c, followed by methylation with methyl iodide to yield 2,3-dimethyl-pyrimidinones 11a–c. The antimicrobial screening showed that many of these compounds have good antibacterial and antifungal activities comparable to streptomycin and fusidic acid used as reference drugs.

ChemInform Abstract: Synthesis of Pyrrole and Indole Quinoxalinone and Oxazinone Derivatives by Intramolecular Copper‐Catalyzed Reactions.

AbstractThe cyclization reactions are carried out by conventional heating or microwave irradiation of pyrrole and indole carboxamides and carboxylates linked with a pendant haloarene.

Synthesis of pyrrole and indole quinoxalinone and oxazinone derivatives by intramolecular copper-catalyzed reactions

Intramolecular N-arylation of pyrrole and indole carboxamides and carboxylates linked with a pendant haloarene by Cu-catalyzed reactions to synthesize pyrrole and indole quinoxalinone and oxazinone derivatives is reported. The ring closure reactions were carried out by conventional heating and MW irradiation. The use of conventional heating affords moderate to good yields of the quinoxalinone and oxazinone derivatives (34-72%), while by using MW heating the best results are obtained (41-99%).

Spectroscopic and photochemical properties of some annulated boldine derivatives

The aim of this study was to determine the influence of the substituent groups on the photostability of eight boldine derivatives, including some oxazole and oxazinone derivatives, in order to increase the sunscreen protection properties previously demonstrated for boldine. Such derivatives showed bands similar to those of boldine in the absorption and emission spectrum. The spectroscopic properties are pH dependent. The photostability of the derivative compounds was higher than that of boldine, in accordance with the low value of the photoconsumption quantum yield determined. The low fluorescence quantum yield values observed for boldine 1 and 4 as both base and hydrochloride derivative compounds led us to postulate that these compounds are deactivated by a mechanism different to the fluorescence pathway, probably due to the electron-withdrawing inductive effect of NO for boldine 1, and to the increase of the aromatic framework for boldine 4.

Synthesis and Reactions of Some New Heterocyclic Compounds Containing Cycloalka[e]thieno[2,3-b]pyridine Moiety

Hydrolysis of ethyl 3-amino-4-aryl-cycloalka[e]thieno[2,3-b]pyridine-2-carboxylates (3a-d) gave the corresponding o-aminocarboxylic acids 4a-d. Heating the latter compounds (4a-d) with acetic anhydride furnished the oxazinone derivatives 5a-d which, in turn, underwent recyclization reaction to give the corresponding pyrimidinones 6a-d upon treatment with ammonium acetate in acetic acid. Reaction of 3-amino-4-aryl-cycloalka[e]thieno[2,3-b]pyridine-2-carboxamides (3f,h) with triethyl orthoformate gave pyrimidinone derivatives 7a,b. Reaction of 3-amino-4-phenyl-cycloalka[e]thieno[2,3-b]pyridine-2-carboxamides 3e,h with aromatic aldehydes furnished tetrahydropyridothienopyrimidinones 8a-d. Chlorination of 7a,b and 6a-d by using phosphorous oxychloride produced 4-chlorocycloalka[5′,6′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine derivatives 9a-f which were used as key intermediates in the synthesis of several new cycloalkapyrido-thienopyrimidines 10a-f˜14a-f. Moreover, some cycloalkapyridothienotriazinones 15a,b-17a,b were synthesized.

Fluorine-containing Heterocycles: Part II Synthesis and Reactions of New Thieno[2,3-b]Pyridine Derivatives Bearing Trifluoromethyl Group

Ethyl [3-cyano-6-(2-thienyl)-4-trifluoromethylpyridin-2-ylthio]acetate (2) and ethyl 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxylate (3) were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with ethyl chloroacetate. The reaction of both 2 and 3 with hydrazine hydrate under different conditions was studied. The main products were [3-cyano-6-(2-thienyl)-4-trifluoromethyl-2-pyridinylthio]acetohydrazide (4) and 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carbohydrazide (5). The condensation of acethydrazide 4 with some aromatic or heterocyclic aldehydes yielded the corresponding hydrazones 6a–d which underwent intramolecular Thorpe–Ziegler cyclisation to give the N1-aryl or heteroaryl-methylene-3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carbohydrazides (7a–d). Treatment of 7a–d with triethyl orthoformate led to the formation of pyridothienopyrimidine derivatives 8a–d. Heating carbohydrazide 5 with acetic acid gave an unexpected product which was assigned as 3-amino-2-methyl-7-(2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5] thieno[3,2-d]pyrimidine-4(3H)-one (12). Moreover, the reaction of 5 with other reagents such as acetic anhydride, formic acid, acetylacetone and/or triethyl orthoformate were carried out and their products were identified. Diazotisation of 5 produced the corresponding acyl azide 18 which underwent Curtius rearrangement to furnish the imidazolone derivative 20. Hydrolysis of the ester 3 gave the aminoacid 21 which in turn was converted into the oxazinone derivatives 22 and 23. Recyclisation of 22 and 23 into some pyrimidinone derivatives (12 and 24–26) was carried out.

Synthesis and Reactions of Some Fused Oxazinone, Pyrimidinone, Thiopyrimidinone, and Triazinone Derivatives with a Thiophene Ring as Analgesic, Anticonvulsant, and Antiparkinsonian Agents.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis and Reactions of Some Fused Oxazinone, Pyrimidinone, Thiopyrimidinone, and Triazinone Derivatives with a Thiophene Ring as Analgesic, Anticonvulsant, and Antiparkinsonian Agents

A series of 2,6-disubstituted pyridine ester derivatives and the corresponding amides were prepared. The esters were hydrolysed to the sodium salts, which were treated with acetic anhydride to afford oxazinone derivatives. These were treated with ammonium acetate to afford 2-methylpyrimidinone derivatives, which were methylated to yield 2,3-dimethylpyrimidinone derivatives. In addition, they were reacted with aniline or hydrazine hydrate to give 3-phenyl- or 3-aminopyrimidinone derivatives. The latter reacted with 2-thiophenecarbaldehyde or phthalic anhydride to afford the corresponding Schiff’s base and imide derivatives. Diazotization of amides gave thienotriazinone derivatives, which were treated with ethyl iodide to afford the corresponding 3-ethyltriazinone derivatives. Also, they were reacted with phenyl isothiocyanate to give the corresponding thiopyrimidinone derivatives, which were alkylated with ethyl iodide or chloroacetic acid to afford the corresponding thioethyl- or thioglycolic acid pyrimidinone derivatives. The pharmacological screening showed that many of these obtained compounds have good analgesic, anticonvulsant, and antiparkinsonian activities comparable to Voltarene®, Carbamazepine®, and Benzotropene® as reference drugs.

ChemInform Abstract: New Oxazinone and Pyrazinone Derivatives as Chiral Reagents for the Asymmetric Synthesis of α-Amino Acids

ChemInform Abstract: New Oxazinone and Pyrazinone Derivatives as Chiral Reagents for the Asymmetric Synthesis of α-Amino Acids

Synthesis and reactions of some 6‐aryl and 2,6‐diaryl‐4‐(4′‐antipyrinyl)‐2,3,4,5‐tetrahydropyridazin‐3‐ones and screening for their antibacterial activities

AbstractSome new pyridazinone derivatives(3) were synthesized through addition of antipyrin to β‐aroylacrylic acids (1) followed by cyclization of the adducts. Reactions of 3 with ethyl bromoacetate, benzenesulfonyl chloride, benzoyl chloride and POCl3 give N‐substituted products and monochlorosubstituted pyridazines (4), respectively. The reactions of the latter with thiourea give unexpected dithio‐derivatives (5), which react with phenylhydrazine to give pyrazolopyridazino pyridazine derivatives (6). Reactions of 2 with NH2OH in ethanol and pyridine afford oxime and oxazinone derivatives 7 and 8, respectively. The antibacterial activities of several compounds were screened.

Stereochemical studies, 145. Saturated heterocycles, 152. Preparation and conformational analysis of stereoisomeric 1,6,7,11b- tetrahydro-2 [formula omitted] [1,3]oxazino [4,3-a]isoquinolin-4-one derivatives

Starting from 1- [bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline 3a, trifunctional 1,2,3,4-tetrahydroisoquinolines were synthetized. From the N -ethoxycarbonyl derivative of 3a, ( r -11b,c-1)-1-hydroxymethyl- (8) and ( r -11b, t -1)-1-chloromethy1-9,10-dimethoxy-1,6,7,llb--tetrahydro-2 H 1,3]oxazino[4,3- a ] isoquinolin-4-one ( 9) were formed in unexpected reactions. High-resolution NMR revealed that the tetrahydroisoquino-line-fused C-1 epimer oxazinone derivatives 8 and 9 have different conformations in solution. The first X-ray diffraction evidence of the presence of two different conformations of oxazinoisoquinolines 8 and 9 in the solid state is provided.