Reaction of 2-(2-oxoethylidene)furan-3(2H)-ones with isopropylidenehydrazides of aromatic carboxylic acids: Synthesis of 3-hydroxy-3-(2-oxoethyl)-2,3-dihydropyridazin-4(1H)-ones

3-Hydroxy-3-(2-oxoethyl)-6-phenyl-2,3-dihydropyridazin-4(1H)-ones were obtained by the reaction of methyl 3-oxo-5-phenylfuran-2(3H)-ylideneacetate or 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one with benzoic or p-nitrobenzoic isopropylidenehydrazides. Equilibrium C₍₅₎H and C₍₅₎H₂ tautomeric forms were detected in solutions of the 4-chlorophenyl derivatives in DMSO-d₆. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1156–1158, August, 2007.     

Synthesis and Anti-HIV-1 Activity of 2-[2-(3,5-Dimethylphenoxy)ethylthio]pyrimidin-4(3H)-ones

New 2-[2-(3,5-dimethylphenoxy)ethyl]thio derivatives of pyrimidin-4(3H)-one containing various substituents at positions 5 and 6 of the pyrimidine ring were synthesized. It was shown that alkylation of 2-thiouracils with 1-bromo-2-(3,5-dimethylphenoxy)ethane in DMF takes place exclusively at the sulfur atom. The obtained 6-benzyl and 6-(2,6-difluorobenzyl) derivatives have clearly defined virus-inhibiting properties with respect to type 1 human immunodeficiency virus in vitro and suppress its reproduction by 50% at concentrations of 1.3 and 11.2 mM respectively.     

A new approach to the facile synthesis of 2-substituted-quinazolin-4(3H)-ones

A new approach to the facile synthesis of 2-substituted-quinazolin-4(3H)-ones and its derivatives using the condensation reaction of substituted 2-aminobenzamide and orthoesters is reported.     

2-芳基-2,3-二氢4(1H)-喹唑啉酮类化合物的合成

在NaHSO4催化下,以苯甲醛和邻氨基苯甲酰胺为底物,在室温下合成了一系列2-芳基-2,3-二氢-4(1H)-喹唑啉酮类化合物,该反应产率高、操作简单、并且避免使用有毒的金属催化剂.     

Synthesis of 2-Benzylidene and 2-Hetarylmethyl Derivatives of 2H-1,4-Benzoxazin-3-(4H)-ones as Neuroprotecting Agents

A wide variety of the title compounds were synthesized by conventional and microwave methods in which the main step is a condensation of an aldehyde with a 1,4-benzoxazin-3-(4H)-one. In all cases, the Z diasteromers were the major products. Of particular importance is the synthesis of novel 2-(3,5-dibromo-4-hydroxy) and 2-(4-acetoxy-3,5-dibromobenzylidene derivatives of 2H-1,4-benzoxazin-3-(4H)-ones, four of which were shown in a previous publication to exhibit potent neuroprotecting properties. The yields of titled compounds ranged from 25 to 83%.     

The green synthesis of 2,3-dihydroquinazolin-4(1H)-ones via direct cyclocondensation reaction under catalyst-free conditions

ABSTRACT

A simple and environmentally benign method is described for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by direct cyclocondensation of 2-aminobenzamide with aromatic aldehydes using water as the reaction medium. The parameters such as temperature, substrate molar ratio and reaction time were examined to establish the optimal synthetic process. The present procedure has advantages of low cost, mild reaction conditions, simple workup process, simply purification, excellent yields and no use of catalyst and hazardous organic solvents.     

A highly enantioselective synthesis of 5-(l-menthyloxy )-4-substituted-3-chloro-2(5H )-furanones

In this paper, stereocontrolled tandem Michael addition-elimination reaction of the novel chiral source, 5-(l-menthyloxy)-3,4-dichloro-2(5H)-furanone, with various thiols and amines has been investigated. A series of new enantiomerically pure compounds, 5–(l-menthyloxy)-4-substituted-3-chloro-2(5H)-furanones, were obtained in good yields with d. e. ? 98% under mild conditions.     

Camps reaction for the synthesis of 3-RS-4-arylquinolin-2-ones

The replacement of the chlorine atom in 2-(chloroacetamido)benzophenones on treatment with RSH (R = Alk, Ar, Hetaryl) in the presence of MeONa is accompanied by intramolecular cyclization following the Camps reaction pattern to give 3-RS-4-arylquinolin-2-ones. Cleavage of 4-aryl-3-(benzoxazol-2-ylthio)quinolin-2-ones by morpholine has resulted in the corresponding 4-aryl-3-mercaptoquinolin-2-ones.     

One-pot synthesis of 3-(2-cyanophenyl)quinazolin-4(3H)-one

Anthranilonitrile reacting with formic acid at room temperature for three days gave 64% of 3-(2-cyanophenyl)quinazolin-4(3H)-one. Under similar conditions anthranilic acid. 4-nitroaniline, and 2,5-dichloroaniline were N-formylated in good yields.Institute of Organic Chemistry and Technology, Silesian Technical University, Krzywoustego, 4, 44–100 Gliwice, Poland; e-mail: wojtex@zeus.polsl.gliwice.pl. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 922–924, July, 2000.     

Photochemical and thermal cyclizations of 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-ones for the synthesis of 4-methylenepyrimidino[5,4-b]indol-2-ones

Photochemical and thermal cyclization of 4-(2-azidophenyl)-3,4-dihydropyrimidin-2-ones could afford fused indoles, such as 1,2,3a,9b-tetrahydro-4-methylenepyrimidino[5,4-b]indol-2-ones and 1,3,5,6,7a,12b-hexahydroquinazolino[9,4-b]indol-2,7-dione in high yields via nitrene electrophilic addition and rearrangement reactions.     

Cytoprotective Activity of Newly Synthesized 3-(Arylmethylamino)-6-Methyl-4-Phenylpyridin-2(1H)-Ones Derivatives

Currently, studies are being conducted on the possible role of the cytoprotective effect of biologically active substances in conditions of cerebral hypoxia or cardiomyopathies. At the same time, oxidative stress is considered one of the important mechanisms of cellular cytotoxicity and a target for the action of cytoprotectors. The aim of this study is to search for derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones. The probability of cytoprotective action was assessed by measuring cell viability using two tests (with neutral red dye and MTT test). It was found that some derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones under the conditions of our experiment had a pronounced cytoprotective activity, providing better cell survival in vitro, including the MTT test and conditions of blood hyperviscosity. To correlate the obtained results in vitro, molecular docking of the synthesized derivatives was also carried out. The standard drug omeprazole (co-crystallized with the enzyme) was used as a standard. It was shown that all synthesized derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones had higher affinity for the selected protein than the standard gastro-cytoprotector omeprazole. The studied derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones also fully satisfy Lipinski’s rule of five (RO5), which increases their chances for possible use as orally active drugs with good absorption ability and moderate lipophilicity. Thus, the results obtained make it possible to evaluate derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones as having a relatively high cytoprotective potential.     

Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones

An efficient, inexpensive, and heterogeneous catalyst, [Al(H₂PO₄)₃], was applied in a three-component, one-pot cyclocondensation reaction of isatoic anhydride with primary amines (or ammonium salts) and aldehydes to afford the corresponding quinazolinone derivatives in excellent yields. Reactions occurred under thermal solvent-free conditions. It was found that this solid acidic catalyst could be easily recovered and reused for at least three cycles without any loss of activity.     

Vitamin B12:An efficient type catalyst for the one-pot synthesis of 3,4,5-trisubstituted furan-2(5H)-ones and N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates

Vitamin B12 was applied as catalyst for the one-pot three-component synthesis of 3,4,5-trisubstituted furan-2(5H)-ones from the condensation between aldehydes, amines and dialkylacetylendicarboxylates at ambient temperature in EtOH. In addition, N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates were synthesised using mentioned catalyst at ambient temperature in EtOH from condensation between formaldehyde, amines, and dialkylacetylenedicarboxylates. This methodology has number of advantages such as:use of green and nonhazardous catalyst, clean work up, short reaction times, high yields and no need to column chromatography.     

邻甲基苯磺酸铜催化一锅法合成3,4-二氢嘧啶-2(1H)-酮

二氢嘧啶酮(DHPMs)及其衍生物具有广泛的生物活性,如抗病毒、抗肿瘤、抗癌、抗高血压及消炎等作用[1].此外,DHPMs及其衍生物作为钙通道阻滞剂、α1a-对抗剂和神经肽Y的对抗剂,显示出良好的药理活性[2].更重要的是,最近几种含二氢嘧啶酮-5-羧酸盐的海洋生物碱被成功分离出来,并表现出重要的生物学性质[3],某些可以阻止HIVgp-120-CD4键的形成,是一种潜在的HIV抑制剂[4].因此,对DHPMs及其衍生物的研究成为生物活性有机杂环化合物的研究热点之一.     

Synthesis and structure of 1,3-dialkyl-4-(sulfonylimino)imidazolidin-2-ones

The reactions of 1,3-dialkyl-4,5-dihydroxyimidazolidin-2-ones with alkyl sulfamides have been studied and previously undescribed 1,3-dialkyl-4-(alkylaminosulfonylimino)imidazolidin-2-ones have been obtained. The structure of 1,3-dimethyl-4-(benzenesulfonylimino)imidazolidin-2-one was investigated by X-ray structural analysis. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1159–1166, August, 2007.     

Acylation of 2-azahetarylacetonitriles with (acetylthio)acetyl and α-(acetylthio)-propionyl chlorides. Production of 5-amino-4-hetarylthiophen-3(2H)-ones

3-Cyano-3-hetaryl-2-oxopropyl-and 3-cyano-3-hetaryl-1-methyl-2-oxopropyl ethanethioates were obtained by the acylation of 2-azahetarylacetonitriles with (acetylthio)acetyl and α-(acetylthio)propionyl chlorides respectively. They are deacetylated by the action of amines and undergo cyclization with the formation of 5-amino-4-hetarylthiophen-2(2H)-ones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1314–1319, September, 2006.     

A facile and environmental friendly strategy for the synthesis of N-methoxyquinolin-2(1H)-ones

A facile and environmental friendly protocol for the construction of N-methoxyquinolin-2(1H)-ones was developed using a stable and easily available N-methoxyquinoline-1-ium tetrafluoroborate as starting material. Due to the mild reaction conditions, a broad range of N-methoxyquinolin-2(1H)-ones with different functional groups have been prepared in reasonable yields.     

高温水中2,3-二氢喹唑啉-4(1H)-酮衍生物的合成反应研究

为发展绿色化学,减少化学反应中有毒害溶剂的使用,本文以高温水为溶剂,在未使用任何有机溶剂及催化剂的条件下,以2-氨基苯甲酰胺与醛为底物,成功合成了2,3-二氢喹唑啉-4(1H)-酮衍生物。研究了反应温度、反应时间及芳环上取代基对反应的影响。在摩尔比1∶1、温度为130℃、反应时间1h的优化条件下,收率为32. 4%～85. 7%。     

Supported N-propylsulfamic acid on magnetic nanoparticles used as recoverable and recyclable catalyst for the synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in water

An efficient and eco-friendly method is reported for the synthesis of 2-substituted-2,3-dihydroquinazolin -4（1 H）-ones from direct cyclocondensation of anthranilamide with aldehydes and ketones using N-propylsulfamic acid supported onto magnetic Fe₃O₄ nanoparticles（MNPs-PSA） as a recoverable and recyclable nanocatalyst in good to excellent yields in water at 70℃.The catalyst was readily separated using an external magnet and reusable without significant loss of their catalytic efficiency.