2-(3-ethyl-2,2-dimethylcyclobutyl-methyl)-4(3H)-quinazolinones

Anthranilic acid and its 5-bromo and 4-chloro derivatives react with pinanoic and pinonoic acid chlorides to give the corresponding N-acyl derivatives. The pinanoyl derivatives give the corresponding 2-(3-ethyl-2,2-dimethyl-cyclobutylmethyl)-4-(3H)-quinazolinones when refluxed in formamide. Pinanoylanthranilic acid reacts with dicyclohexylcarbodiimide to give 2-(3-ethyl-2,2-dimethylcyclobutylmethyl)benz-3,1-oxazin-4(H)-one and subsequently with hydrazine hydrate to give 3-amino-2-(3-ethyl-2,2-dimethylcyclobutylmethyl)-4(3H)-quinazolinone. Refluxing of the pinanoyl- and pinonoylanthranilic acids with acetic anhydride gives acetylanthranilic acid, and pinonoylanthranilic acid gives 4(3H)-quinazolinone with formamide.Riga Technical University, Riga LV-1658, Latvia; e-mail: marina@osi.lanet.lv. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 811–817, June, 1999.     

Novel Diels-Alder reaction of 4-nitro-1(2H)-isoquinolones

A novel Diels-Alder (DA) reaction with 4-nitro-1(2H)-isoquinolones acting as the dienophile afforded 5(6H)-phenanthridone derivatives. The DA reaction of 4-nitro-1(2H)-isoquinolone with 1-methoxy-1,3-butadiene gave biologically active 5(6H)-phenanthridone possessing in a high yield. Regioselectivity of 4-nitro-1(2H)-isoquinolones with 1-methoxy-3-silyloxy-1,3-butadiene was calculated using molecular orbital (MO) calculations.     

2-(3-Acetylamino-2,2-dimethylcyclobutyl)-methyl-4(3H)-quinazolinones

Beckmann rearrangement of N-[3-(1-hydroxyimino)ethyl-2,2-dimethylcyclobutyl]acetylanthranilic acid, and its 5-bromo and 4-chloro derivatives gives the corresponding N-(3-acetylamino-2,2-dimethylcyclobutyl)acetylanthranilic acids. Treatment of these acylanthranilic acids with formamide gives 2-(3-acetylamino-2,2-dimethylcyclobutyl)methyl-4(3H)-quinazoline and its 6-bromo and 7-chloro derivatives.     

4-氧代-3（4H）-喹唑啉-5-羧酸的合成

以2-氨基-6-甲基苯甲酸为起始原料,通过合环反应生成两种4-氧代-3(4H)-喹唑啉-5-羧酸衍生物(1a, 1b), 1a, 1b分别经高锰酸钾氧化合成了4-氧代-3(4H)-喹唑啉-5-羧酸（2a, 2b）,其结构经¹H NMR, ¹³C NMR和MS表征。研究了投料比｛r［n(高锰酸钾) :n(5-甲基-3(4H)-喹唑啉-4-酮)］｝和反应温度等对收率的影响。结果表明：在最佳反应条件（r=7:1,中性高锰酸钾氧化,于90 ℃反应）下合成2总收率可达66%。     

Thermal-Induced Dimerization Cyclization of Ethyl N-(Styrylcarbamoyl)acetates: Formation of 4-Hydroxy-2(1H)-pyridone-3- carboxamide Derivatives

Thermal-induced dimerization cyclization of ethyl N-(styrylcarbamoyl)acetate derivatives has been investigated, leading to 4-hydroxy-2(1H)-pyridone-3-carboxamide derivatives with good yields in diphenyl ether on 200–210 °C. Ethyl N-(styrylcarbamoyl)acetate derivatives readily provided the intermolecular cyclization products 4-hydroxy-2(1H)-pyridone-3-carboxylates on reflux in xylene. In addition, several related 3-acetyl-4-hydroxy-5-phenylpyridin-2(1H)-ones have been prepared. It provided an efficient preparation of 4-hydroxy-2(1H)-pyridone-3-carboxamide derivatives.     

5-(S)-孟氧基-3,4-二卤-2(5H)-呋喃酮与4-硝基邻苯二胺的Michael加成―消除反应

在Et3N作为碱的温和条件下,5-(S)-孟氧基-3,4-二卤-2(5H)-呋喃酮与芳香胺4-硝基邻苯二胺发生串联的Michael加成―消除反应,生成了新的含有苯环结构的5-孟氧基-4-氨基-3-卤-2(5H)-呋喃酮类化合物。新化合物的结构通过紫外―可见光谱(UV-Vis)、红外光谱(IR)、质谱(MS)、核磁共振氢谱(1H NMR)、核磁共振碳谱(13C NMR)和元素分析等表征证实。该多环结构卤代2(5H)-呋喃酮化合物的合成,能为某些多官能团的结构复杂的2(5H)-呋喃酮化合物的合成提供新途径。     

Heterocyclic studies—XXIV: Mass spectra of some pteridin-4(3H)-ones and 3-methoxypteridin-4(3H)-ones

Mass spectra of pteridin-4(3H)-one and all its mono-, di- and tri-C-methyl derivatives are recorded. Spectra of 3-methoxypteridin-4(3H)-one and four of its mono- and dimethyl derivatives are also recorded. Pteridin-4(3H)-one fragments mainly by loss of CO and HCN in either order. Methyl substitution in the pyrazine ring leads to that ring fragmenting in preference to the oxygen bearing pyrimidine ring. Elucidation of fragmentation pathways was facilitated by changes in peak positions with changing methyl substitution patterns. 3-Methoxypteridin-4(3H)-ones fragment mainly through initial loss of CH₂O, but the ions so produced break down differently from isomeric molecular ions of pteridin-4(3H)-ones. Several fragmentation pathways are discussed.     

6,7-二氧亚甲基-3-氮杂(硫杂)-1(2H,4H)吖啶酮及其衍生物的合成

氮杂吖啶酮;硫杂吖啶酮;杂环化合物;6;7-二氧亚甲基-3-氮杂(硫杂)-1(2H;4H)吖啶酮及其衍生物的合成     

Green Route for the Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-ones Using GO@Fe(ClO4)3 Nanocatalyst under Solvent-Free Conditions

Russian Journal of Organic Chemistry - An effective and environmentally benign methodology has been proposed for the synthesis of isoxazol-5(4H)-one derivatives using GO@Fe(ClO4)3 nanocatalyst. The...     

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 in vitro antibacterial activities of 7-(3-aminopyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)quinolone derivatives

<正>A series of novel 7-(3-aminopyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-y1)quinolone derivatives were designed,synthesized and evaluated for in vitro antibacterial activities.Compounds 6g,7g and 7h with the potencies similar to those of gemifloxacin, moxifloxacin,gatifloxacin and levofloxacin against Gram-positive organisms,worth further investigation.     

A CONVENIENT SYNTHESIS OF NEW PYRIDOTHIENOPYRIMIDIN-4 (3H) ONES AND PYRIDOTHIENOPYRIMIDIN-2, 4(1H, 3H) DIONES

New derivatives of 2-substituted pyrido[3′,2′:4,5]thieno[3,2-d]pyri-midin-4(3H) ones and 3-substituted pyrido[3′,2′:4,5]thieno[3,2-d]pyri-midin-2,4(1H,3H) diones have been prepared by base catalyzed cyclocondensation of ethyl-3-aminothieno[3,2-b]pyridine-2-carboxylate with aryl nitriles and aryl- or alkyl isocyanates respectively.     

From calcium interaction to calcium electrochemical detection by [(C5H5)Fe(C5H4COCH=CHC6H4NEt2)] and its two novel structurally characterized derivatives

[(C(5)H(5))Fe(C(5)H(4)COCH=CHC(6)H(4)NEt(2))] (1) has been electrochemically evaluated toward different cations in solution. Calcium sensing by this compound and its two new derivatives [(C(5)H(5))Fe(C(5)H(4)CO(CH=CH)(2)C(6)H(4)NMe(2))] (2) and [(C(5)H(5))Fe(C(5)H(4)CH=CHCOCH=CHC(6)H(4)NEt(2))] (3) that exhibit a conjugated link between the ferrocene unit and the nitrogen atom has been thoroughly examined. Compounds 2 and 3 have been structurally characterized by single-crystal X-ray diffraction studies. The three related protonated species [1H][BF(4)] (4), [2H][BF(4)] (5), and [3H][BF(4)] (6) have been isolated in a good yield. NMR experiments clearly established that calcium interaction occurs in the vicinity of the carbonyl group, and mass spectrometry studies confirmed that this interaction, which involves several ligand-Ca(2+) adducts, is complex. A combination of electrochemical and NMR experiments highlighted an original salt influence on the electrochemical calcium sensing result.     

Synthesis of 2-(2-arylamino-3-alkyloxazolidynyl-4)- and 2-(2-arylamino-3-alkylthiazolidynyl-4-N-alkylacetamides from 2(5H)-furanone

Aminolysis of 2(5H)-furanone leads to 3-alkylamino-4-hydroxy-N-alkylbutyramides which easily form hydroxy derivatives of thiourea. The latter, depending on the protonation or quaternization site, easily undergo cyclization to thiazolidine and oxazolidine derivatives.Translated from Khimiya Geterotsiklicheskilch Soedinenii No. 12, pp. 1629–1632, December, 1985.     

One Pot Synthesis of 3-Aryl, 4-Methyl 2(5H)-Furanones

A series of 3-aryl, 4-methyl 2(5H)-furanones variably subtituted in the phenyl ring were conveniently prepared in one pot in good yields from the corresponding phenylacetic acid derivatives and chloroacetone.     

Substituted 4(5H)-oxazolones and their salts. 3. Synthesis of 4(5H)-oxazolonium salts from amides of 2,4-dihydroxy-3,3-dimethylbutanoic acid

2-Alkyl-substituted 4(5H)-oxazolonium salts were synthesized by the reaction of amides of 2,4-dihydroxy-3,3-dimethylbutanoic (pantoic) acid with aliphatic carboxylic acid anhydrides in the presence of an equimolar amount of perchloric acid. The hydrolysis of these salts was realized. Various acyl derivatives of pantoic acid amides were obtained, and the possibility of their cyclization to give 4(5H)-oxazolonium salts under the influence of condensing reagents was demonstrated. The mechanism of the heterocyclization of pantoic acid amides is discussed on the basis of these results.See [1] for communication 2.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 894–900, July, 1981.     

Pyridine-2-thionate as a versatile ligand in Pd(II) and Pt(II) chemistry: the presence of three different co-ordination modes in [Pd2(micro2-S,N-C5H4SN)(micro2-kappa2S-C5H4SN)(micro2-dppm)(S-C5H4SN)2

Reactions of [MCl2(L-L)], M = Pt, Pd; L-L = bis(diphenylphosphino)methane (dppm) or bis(diphenylphosphino)ethane (dppe), with NaC5H4SN in a 1 : 2 molar ratio lead to mononuclear species [M(S-C5H4SN)2(P-P)], M = Pt; L-L = dppm (1) or dppe (2) and M = Pd; L-L = dppe (3), as well as to the dinuclear [Pd2(micro2-S,N-C5H4SN)(micro2-kappa2S-C5H4SN)(micro2-dppm)(S-C5H4SN)2] (4). In contrast, reaction of [MCl2(dppm)] with NaC5H4SN in a 1 : 1 molar ratio leads to [Pd2(micro2-S,N-C5H4SN)3(micro2-dppm)]Cl (5) and trans-[Pt(S-C5H4SN)2(PPh2Me)2] (6) respectively. The latter is formed in low yield by cleavage of the dppm ligand. The dinuclear derivatives 4 and 5 present an A-frame and lantern structure, respectively. The former showing three different co-ordination modes in the same molecule with a short Pd-Pd distance of 2.9583 (9) A and the latter with three bridging S,N thionate ligands showing a shorter Pd-Pd distance of 2.7291 (13) A. Both distances could be imposed by the bridging ligands or point to some sort of metal-metal interaction.     

Reactions of 6-benzyl-5-methyl-2-(methylsulfanyl)pyrimidin-4(3H)-one with aliphatic and aliphatic-aromatic amines

Russian Journal of Organic Chemistry - The rules were investigated of the regioselective synthesis of N2-substituted derivatives of 2-amino-6-benzyl-5-methylpyrimidin-4(3H)-one from...     

Alkylation and Acylation of 1-(4-Phenylaminophenyl)dihydropyrimidine-2,4-(1H,3H)-diones

The C- and N-substituted derivatives of 1-(4-phenylaminophenyl)dihydropyrimidine-2,4-(1H,3H)-diones have been obtained by alkylation and acylation. The secondary amino group takes part in the acylation reaction, before the amide group of the heterocycle.     

Novel hetero-bimetallic metalla-macrocycles based on the bis-1-pyridyl ferrocene [Fe(eta 5-C5H(4)-1-C5H4N)2] ligand. Design,synthesis and structural characterization of the complexes [Fe(eta 5-C5H(4)-1-C5H4N)2](AgI)2(2+)/(CuII)2(4+)/(ZnII)2(4+)

The bidentate sandwich ligand [Fe(eta 5-C5H(4)-1-C5H4N)2] has been prepared, structurally characterized and employed in the preparation of the novel supramolecular heterobimetallic metalla-macrocycles [Fe(eta 5-C5H(4)-1-C5H4N)2]Ag2(NO3)(2).1.5H2O, [Fe(eta 5-C5H(4)-1-C5H4N)2]Cu2(CH3COO)(4).3H2O and [Fe(eta 5-C5H(4)-1-C5H4N)2]Zn2Cl4.