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Sarah J.P. Yoon-Miller 《Tetrahedron letters》2007,48(5):827-830
A three step, convergent synthesis of 4-aryl-3-pyrrolin-2-ones from a tetramic acid has been developed. The key transformation utilized a Suzuki-Miyaura cross-coupling reaction between a 4-tosyloxy-3-pyrrolin-2-one and an arylboronic acid. This work also provides access to 4-arylpyrrolidin-2-ones, cyclic analogs of γ-aminobutyric acid (GABA). Hydrogenation of 4-(4′-chlorophenyl)-3-pyrrolin-2-one proceeded smoothly to give baclofen lactam. 相似文献
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以2-氨基-4-三氟甲基-5-甲基-噻吩-3-羧酸乙酯(1)为起始原料制得膦亚胺2.在碳酸钾的催化下,膦亚胺2与芳基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上2,2’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]3;膦亚胺2与烷基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上3,3’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]4.化合物3的核磁共振氢谱表明关环反应在嘧啶环的2,2’位;化合物4的核磁共振氢谱表明关环反应在嘧啶环的3,3’位.对合成反应机理的推导及目标产物核磁共振氢谱数据的分析解释了此合成反应的选择性. 相似文献
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A. A. Bogolyubov N. B. Chernysheva V. V. Nesterov M. Yu. Antipin V. V. Semenov 《Chemistry of Heterocyclic Compounds》2004,40(10):1305-1309
The dehydration of two 5,5-disubstituted 4-hydroxy-4-methyl-3-phenylaminooxazolidin-2-ones into the corresponding 4-methylene-3-phenylaminooxazolidin-2-ones has been carried out. The structure of the products was confirmed by X-ray diffraction analysis.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1512–1517, October, 2004. 相似文献
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We herein describe the discovery of a mild, one-pot tandem acylation-cyclization for the synthesis of 4-amino-3-benzimidazol-2-ylhydroquinolin-2-ones from 2-aminobenzenecarbonitriles and ethyl 2-benzimidazol-2-yl acetates. 相似文献
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Abstract Thiazolidin-4-ones are known to exhibit diverse biological activities such as antimicrobial, anticancer, antidiarrheal, anticonvulsant, antidiabetic, antihistaminic, and antifungal activities. In the present investigation, a series of 2-haloacetamides was prepared by reacting chloroacetyl chloride with amines in dry benzene under reflux conditions. The formed 2-haloacetamides reacted with potassium thiocyanate in refluxing dry acetone to afford new 2-iminothiazolidin-4-ones. The 5-arylidene-2-imino-3 (napthalen-2yl)-thiazolidin-4-ones were prepared by condensing 2-iminothiazolidin-4-ones with substituted benzaldehydes. All the products were characterized by infrared, mass, and 1H and 13C NMR techniques. 相似文献
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P. Paradesi Naidu Akula Raghunadh K. Raghavendra Rao Ramamohan Mekala J. Moses Babu B. R. Rao 《合成通讯》2014,44(10):1475-1482
Urea/thiourea have been identified as an effective ammonia surrogate in the construction of quinazolin-4(3H)-one ring. This strategy afforded a simple and catalyst-free synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones via the reaction of isatoic anhydride and aryl aldehydes in the presence of urea or thiourea in ethanol. The reaction proceeded well to afford the quinazolin-4(3H)-one or its dihydro derivative, depending on the nature of carbonyl compounds employed. 相似文献
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Synthesis of 6- and 7-substituted benzoxazin-3-ones was already described in the literature by acylation of the corresponding benzoxazin-3-ones or cyclization of the corresponding 4- or 5-acyl-2-aminophenols. This paper describes original synthetic pathways to afford the 6- and 7-acyl products in the benzothiazin-3-one series, respectively, via Stille coupling reaction and by acylation. 相似文献
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A novel and unexpected ring-expansion reaction of 1,2-benzisoxazol-3-ones is identified. The scope of this reaction is exemplified and the proposed mechanism is also implicated in another degradation process. This reaction also represents a new method for accessing the 4H-1,3-benzoxazin-4-one skeleton. 相似文献
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A. T. Soldatenkov A. W. Temesgen K. B. Polyanskii I. A. Bekro S. A. Soldatova A. A. Pupov N. D. Sergeeva 《Chemistry of Heterocyclic Compounds》2001,37(7):844-849
One-reactor oxidation by potassium permanganate has been carried out for a series of 4-aryl- and 4-methyl-1,2,3,6-tetrahydropyridines to give 1-formylamino-substituted 3-arylpropan-3-ones and butan-3-ones. The effect has been studied of the nature of the substrate, the temperature, and interphase transfer catalysts on the yield of amino alkanone. It is proposed that the reaction proceeds through the intermediate formation of 3,4-dihydroxypiperidin-2-ones which then undergo oxidative decyclization with elimination of one carbon atom. 相似文献
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Reaction of arylmethylidene derivatives of furan-2(3H)-one with ethyl diazoacetate is accompanied by elimination of nitrogen and leads to the substituted pyran-3(2H)-ones.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2049–2050, October, 2007. 相似文献
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Synthesis of several 3,3-diarylazepan-4-ones and 5,5-diarylazepan-4-ones has been established starting from two tetrasubstituted olefins, which is derived from commercially available piperidine-3-carboxylic acid ethyl ester and piperidine-4-carboxylic acid ethyl ester. The single isomer with the structural skeleton of 3,3-diarylazepan-4-one and 5,5-diarylazepan-4-one is constructed in two functional group transformations of Grignard addition/dehydration and epoxidation/pinacol rearrangement. 相似文献
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Sergii Golota Ivan Sydorenko Roman Surma Olexandr Karpenko Andrzej Gzella 《合成通讯》2017,47(11):1071-1076
A multicomponent synthetic approach for 5-aryl/heterylidene-2-(2-hydroxyethylamino)- and 2-(3-hydroxypropylamino)-thiazol-4-ones starting from 2-thioxothiazolidin-4-one or 2-methylsulfanylthiazol-4-one was developed. The proposed method involves simultaneous aminolysis of 2-thioxo- or 2-methylsulfanyl groups and Knoevenagel condensation with (hetero)aromatic aldehydes using 2-aminoethanol or 3-aminopropan-1-ol as catalysts. Side-chain prototropic amino–imino tautomerism was observed for target 5-ylidene-2-alkylaminothiazol-4-ones. 相似文献
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V. I. Kelarev M. A. Silin I. G. Kotova K. I. Kobrakov I. I. Rybina V. K. Korolev 《Chemistry of Heterocyclic Compounds》2003,39(2):213-222
Condensation of the N-(3,5-dichloropyridyl-2)- and N-(benzothiazolyl-2-thioacetyl)hydrazones of carbonyl compounds with thioglycolic acid gave the 3-(3,5-dichloropyridyl-2)amino- and 3-[N-(benzothiazolyl-2-thioacetyl)amino]-2-R1-2-R2-thiazolidin-4-ones. Reaction of 1-(benzothiazolyl-2-thioacetyl)-4-R-thiosemicarbazides with chloroacetic acid in the presence of sodium acetate gave the 2-[N-(benzothiazolyl-2-thioacetyl)hydrazono]-3-R-thiazolidin-4-ones. It was found that the N-(benzothiazolyl-2-thioacetyl)hydrazones, both in the solid state and in solution, exist in the form of an equilibrium mixture of the EZ'- and EE'-isomers as a result of hindered rotation around the amide N-CO bond. 相似文献
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Isothiocyanate 2, obtained from aza-Wittig reaction of iminophosphorane 1 with CS2, reacted with amine to give 2-thioxo-2,3,5,6,7,8-hexahydrobenzothieno[2,3-d]pyrimidin-4(1H)-ones 4 in the presence of sodium ethoxide. S-Alkylation of 4 produced 2-alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones 5 in good yields. 相似文献
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喹唑啉-4(3H)-酮是一类生物碱,取代喹唑啉-4(3H)-酮具有广泛的药理学活性.因而对其合成方法和合成新型喹唑啉-4(3H)-酮的衍生物的研究已成为热点.低价钛试剂是一种还原偶联试剂,它能引起醛酮的还原偶联生成烯烃,还能引起其它官能团的还原偶联反应,该反应已应用于天然产物和一些碳环化合物的合成,而用于杂环化合物的合成研究报道较少.本文报道低价钛试剂(TiCl4-Zn体系)促进的1,2-二氢喹唑啉-4(3H)-酮的合成。 相似文献
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The general synthesis and a novel intramolecular nucleophilic aromatic substitution (SNAr) reaction of 2-carboxamido-3-arylquinazolin-4-ones, a potentially useful scaffold in the field of medicinal chemistry, are described. The synthetic utility of the SNAr reaction as a tool for the synthesis of secondary aryl amines, including diaryl amines, is also demonstrated. 相似文献