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1.
N, N-Disubstituted 5-arylmethylidene-2-aminothiazol-4(5 H)-ones reacted with diethyl malonate, ethyl benzoylacetate, acetylacetone, or cyclopentadiene in refluxing toluene and in presence of powdered sodium to give the respective 5-arylmethylidene-2′-amino-2,5′-bithiazolylidene-4,4′-dione derivatives in moderate yields. 5-Benzylidene-2-morpholin-4-yl-2-thiazol-4(5 H)-one reacted with malononitrile in toluene and in presence of powdered sodium under mild conditions to afford the 1:1 adduct, benzylmalononitrile, and 2-morpholin-4-yl-2-thiazol-4(5 H)-one. However, similar treatment of 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5 H)-one with malononitrile yielded the 2,5′-bithiazolylidene-4,4′-dione derivative together with 4-methoxyphenylmethylidene malononitrile. Treatment of 5-benzylidene- and 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5 H)-ones with 3-phenyl-4-oxo-2-thioxo-1,3-thiazolidine in refluxing toluene and in presence of powdered sodium produced 5-arylmethylidene-3-phenyl-4-oxo-2-thioxo-1,3-thiazolidines in good yields. The structures of all products were deduced from microanalytical and spectroscopic data, mechanistic details are discussed. 相似文献
2.
2-alkylthio-3-alkyl-5-arylmethylidene-4H-imidazol-4-ones were synthesized by the S-alkylation and N-alkylation of 2-thioxo-5-arylmethylidene-4-imidazolidinones, which were obtained via a tandem aza-Wittig reaction of vinyliminophosphoranes, carbon disulfide, and excess ammonium hydroxide (28% NH 3 in water). 相似文献
3.
3-Amino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-ones were converted into 2-aryl-5H-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-ones
on treatment with carboxylic acids and POCl 3. 3-Arylmethylidenamino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-ones also cyclized to 2-aryl-5H-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-ones
when oxidized with potassium chlorate in acetic acid, but on heating they were deaminated to give 2-thioxo-1,2,3,4-tetrahydroquinazolin-4-one
and aryl nitriles.
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Translated from Khimiya Geteotsiklicheskikh Soedinenii, No. 5, 787–791, May, 2006. 相似文献
4.
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
5.
Methyl 1-bromocyclopentanecarboxylate and methyl 1-bromocyclohexanecarboxylate reacted with zinc and 2-arylmethylidene-2,3-dihydro-1 H-inden-1-ones or 2-arylmethylidene-3,4-dihydronaphthalen-1(2 H)-ones to give 4′-aryl-4′,5′-dihydro-2′ H-spiro[cyclopentane(cyclohexane)-1,3′-indeno[1,2- b]pyran]-2′-ones or 4-aryl-5,6-dihydrospiro[benzo[ h]chromene-3,1′-cyclopentane(cyclohexane)]-2(4 H)-ones, respectively. 相似文献
6.
Addition of 1,3,3-trimethyl-3,4-dihydroisoquinolines to N-benzylideneanilines gives substituted N-[2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-1-phenylethyl]anilines, whereas 2′,5′,5′-trimethyl-4′,5′-dihydro-4 H-spiro[naphthalene-1,3′-pyrrol]-4-one reacts with N-benzylideneanilines along two pathways involving cyclization to substituted 2,3,3a,4,10,11-hexahydrobenzo[ f]pyrrolo[2,3- d]quinolin-5(1 H)-ones or elimination of the aniline residue with formation of substituted 5′,5′-trimethyl-2-styryl-4′,5′-dihydro-4 H-spiro[naphthalene-1,3′-pyrrol]-4-ones. 相似文献
7.
Formation of Methyl 5,6-Dihydro-l, 3(4 H)-thiazine-4-carboxyiates from 4-Allyl-l, 3-thiazol-5(4 H)-ones . The reaction of N-[1-( N, N-dimethylthiocarbamoyl)-1-methyl-3-butenyl]benzamid ( 1 ) with HCl or TsOH in MeCN or toluene yields a mixture of 4-allyl-4-methyl-2-phenyl-1,3-thiazol-5(4 H)-one ( 5a ) and allyl 4-methyl-2-phenyl-1,3-thiazol-2-yl sulfide ( 11 ; Scheme 3). Most probably, the corresponding 1,3-oxazol-5(4 H)-thiones B are intermediates in this reaction. With HCl in MeOH, 1 is transformed into methyl 5,6-dihydro-4,6-dimethyl-2-phenyl-1,3(4 H)-thiazine-4-carboxylate ( 12a ). The same product 12a is formed on treatment of the 1,3-thiazol-5(4 H)-one 5a with HCl in MeOH ( Scheme 4). It is shown that the latter reaction type is common for 4-allyl-substituted 1,3-thiazol-5(4 H)-ones. 相似文献
8.
4-Alkylamino-2(1 H)-pyridinethiones ( 1) react with bis-trichlorphenylethylmalonate ( 3) to give four isomeric products: 5-thioxo-1,6-naphthyridine-2(1 H)-ones ( 4), 7,7-dimethyl-4 H-thiopyrano[2,3-b]pyridine-4-ones ( 6), 2,2-dimethyl-2 H-thiopyrano[2,3-b]pyridine-5,7-dioles ( 7) and 2,2-dimethyl-2 H-thiopyrano[2,3-b]pyridine-5(3 H)-ones ( 8). On treatment with alkali the thioxogroup of 4 is hydrolyzed and 1,6-naphthyridinediones ( 5) are formed. Compound 5 can also be synthesized by heating the alkylaminopyridones ( 2) together with 3. 6 can be hydrolyzed to 2-thioxo-3-pyridylpropylketones ( 12). On treatment with diluted alkali or conc. acid the aminogroup of 7 and 8 is hydrolyzed and 10 is formed. By heating in 20% NaOH 10 is transformed to the dihydroxymercapto-3-pyridylmethylketone ( 11). Herrn Prof. Dr.Erich Ziegler mit den besten Wünschen zum 70. Geburtstag gewidmet. 相似文献
9.
The reaction of 6-(R-amino)-5-acetyl-4-methylsulfonyl-2-phenylpyrimidines with amines was studied. 6-Arylamino derivatives react with alkylamines to form 6-alkylamino-4-arylamino-5-acetyl-2-phenylpyrimidines, which upon refluxing in benzene with dimethylformamide dimethylacetal are converted to 4-alkylamino-8-aryl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-ones. The cyclization proceeds selectively with participation of the arylamino group only, the alkylamino group being not involved. At the same time, refluxing of 5-acetyl-4,6-dibenzylamino-2-phenylpyrimidine with dimethylformamide dimethylacetal in toluene affords the product of condensation on the acetyl group, which upon refluxing in o-xylene transforms to 4-benzylamino-8-benzyl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-one. 相似文献
10.
2-R-5-Imino-6 H-1,3,4-thiadiazolo[3,2- a]pyrimidin-7-ones react with aromatic and heterocyclic aldehydes in the presence of Et 3N to give condensation products on the methylene group, which react with carbon disulfide to yield the corresponding 2,6-disubstituted
8-thioxo-9,9a-dihydro-1,3,4-thiadiazolo[3′,2′∶1,2]pyrimidino[5,6- d]1,3-thiazin-5-ones.
Deceased.
Translated from Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 366–368, February, 1999. 相似文献
11.
Treatment of N-methylmorpholinium 4-R-6-amino-3,5-dicyano-1,4-dihydropyridine-2-thiolates (R = 2-ClC 6H 4 and 2-MeOC 6H 4) with primary amines in the presence of an excess of formaldehyde gave 13-R-8-thioxo-3,5,7,11-tetraazatricyclo[7.3.1.0 2,7]tridec-2-ene-1,9-dicarbonitrile derivatives in high yields (66–95%). In a similar way, aminomethylation of 3-R-10-amino-7,11-dicyano-9-aza-3-azoniaspiro[5.5]undeca-7,10-diene-8-thiolates
(R = Me and Et) afforded 1′-alkyl-8-thioxospiro[3,5,7,11-tetraazatricyclo[7.3.1.0 2,7]tridec-2-ene-13,4′-piperidine]-1,9-dicarbonitriles in 43–91% yields. Alternatively, these compounds were obtained by multicomponent
cyclocondensation of N-alkylpiperidin-4-ones, cyanothioacetamide, primary amines, and aqueous formaldehyde. The starting 3-R-10-amino-7,11-dicyano-9-aza-3-azoniaspiro[5.5]undeca-7,10-diene-8-thiolates
were prepared by a new method from N-alkylpiperidin-4-ones and cyanothioacetamide. The structure of 5,11-bis(4-ethoxyphenyl)-13-(2-methoxyphenyl)-8-thioxo-3,5,7,11-tetraazatricyclo[7.3.1.0 2,7]tridec-2-ene-1,9-dicarbonitrile was examined by X-ray diffraction analysis.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1014–1022, May, 2007. 相似文献
12.
A series of new N- and S-substituted 1,3,4-oxadiazole derivatives were synthesized. 5-Pyridin-3-yl-3-[2-(5-thioxo-4,5-dihydro-l,3,4-thiadiazol-2-yl)ethyl]-1,3,4-oxadiazole-2(3 H)-thione and 5-[(5-(pyridin-3-yl)-1,3,4-oxadiazol-2-ylthio)methyl]- N-phenyl-1,3,4-thiadiazol-2-amine were formed by cyclization of 3-(5-pyridin-3-yl-2-thioxo-1,3,4-oxadiazol-3(2 H)-ylpropanimidohydrazide and 2-[(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)thio]thiosemicarbazide with CS 2 and H 2SO 4. On the other hand, a number of new bicyclic 1,2,4-triazolo[3,4- b][1,3,4]thiadiazole derivatives were synthesized. 6-Pyridin-3-ylbis[1,2,4]‐triazolo[3,4- b:4′,3′- d][1,3,4]thiadiazole-3(2 H)-thione was synthesized by reaction of 6-(hydrazino)-3-pyridine-3-yl[1,2,4]triazolo[3,4- b][1,3,4]thiadiazole with CS 2/KOH/ EtOH. The structures of the newly synthesized compounds were elucidated by the spectral and analytical data IR, Mass, and 1H NMR spectra.
Correspondence: Adel A.-H. Abdel-Rahman, Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koam,
Egypt; Wael A. El-Sayed, National Research Centre, Department of Photochemistry, Cairo, Egypt. 相似文献
13.
A new convenient method for the synthesis of 6-amino-2 H,4 H-pyrano[2,3- c]pyrazole-5-carbonitriles, namely, four-component condensation of carbonyl compounds (aromatic aldehydes, heterocyclic ketones),
malononitrile, β-keto esters, and hydrazine hydrate in ethanol in the presence of triethylamine as a catalyst, which occurs
selectively, is developed. One-pot two-step modification of this method is proposed for the synthesis of spiro[(3 H)-indole-3,4 ′-(4′ H)-pyrano[2,3- c]pyrazol]-2-ones. 相似文献
14.
The interaction of sulfonamides with 4,5-dihydroxyimidazolidin-2-ones was studied for the first time. The earlier unknown
4,4′-sulfonyldiiminobis(1,3-dialkylimidazolidin-2-ones) and 4(5)-aryl(alkyl)-sulfonyliminoimidazolidin-2-ones were synthesized.
A probable pathway of the reaction was proposed. 1,3-Diethyl-4,5-dihydroxyimidazolidin-2-one was isolated and described.
Translated from Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1604–1607, August, 1998. 相似文献
15.
Summary. N′-Arylacetonitrilimines were generated from acetohydrazonyl chlorides and reacted with mercaptoalkanoic acids forming 4-aryl-5-oxo-3-thiahexanoic
acids. These were cyclized by reaction with dicyclohexyl carbodiimide yielding 2-acetyl-4-aryl-6 H-1,3,4-thiadiazin-5-ones.
Received November 13, 2001. Accepted January 9, 2002 相似文献
16.
Reflux of 3-cyanothiochromone with benzylamine in toluene afforded 17-benzyl-6,7,14,15-tetrahydro-7,15-epiminobis(8 H,16 H-dithiochromeno)[2,3- b:2′,3′- f][1,5]diazocine-6,14-dione, the self-condensation product of 2-amino-3-(benzyliminomethyl)thiochromone. Similar reaction with
phenethylamine leads to 2-(thiochromon-3-yl)-5 H-thiochromeno[2,3- d]-pyrimidin-5-one. Mechanism of formation of the dimeric products was considered. 相似文献
17.
The intramolecular electrophilic substitution in 6-functionalized 1,3-dimethyl-1 H-pyrrolo[3,4- d]pyrimidine-2,4(3 H,6 H)-diones was used for the synthesis of pyrimido[4′,5′:3,4]-pyrrolo[1,2- a]quinoxaline-8,10(7 H,9 H)-dione, pyrimido[4′,5′:3,4]pyrrolo[2,1- c][1,2,4]benzo-triazine-8,10(7 H,9 H)-dione, and 2 H-pyrimido[4′,5′:3,4]pyrrolo[1,2- a]indole-2,4,11(1 H, 3 H)-trione derivatives.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2180–2185, December, 2006. 相似文献
18.
Three-component condensation of benzooxazol-2-yl-, benzothiazol-2-yl-, and 5-ethoxycarbonyl-4-methyl-1,3-thiazol-2-ylguanidines
with orthoesters and aroylacetonitriles afforded 4-aryl-5-cyano-2-hetarylaminopyrimidines.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1049–1050, June, 2006. 相似文献
19.
6-Methoxy-2-methylpyridazin-3(2 H)-one ( 1 ) gave with 2-diazopropane ( 8 ) a mixture of 3 H-pyrazolo[3,4- d]-pyridazin-4(5 H)-one derivative 12 , as the main product, and -7(6 H)-one derivative 10 , as the minor product. On the other hand, 4-substituted pyridazin-3(2 H)-ones 2, 3 , and 4 gave 3 H-pyrazolo[3,4- d]pyridazin-7(6 H)-one 10 , exclusively, while 5-substituted pyridazin-3(2 H)-ones 5, 6 , and 7 produced only the isomeric 3 H-pyrazolo[3,4- H]pyridazin-4(5 H)-one 12 . The 5-phenylsulfonyl derivative 13 gave with 8 by elimination of a molecule of nitrogen, followed by rearrangement, 1,2-diazepine derivative 15 and with an excess of 8 3 H-pyrazolo[3,4- d][1,2]diazepine derivative 16. 1 ,2-Dimethylpyridazine-3,6-(1 H,2 H)-dione and its derivatives 18 and 19 produced 3 H-pyrazolo[3,4- d]pyridazine-4,7(5 H,6 H)-dione derivative 23 , while from 17 and 1-diazoindane ( 24 ) the spiro compound 27 was obtained. The 1,2-dihydro and 3a,7a-dihydro intermediates 21 and 25 were isolated. 相似文献
20.
8-Substituted 2-morpholin-4-yl-quinolin-4-ones and 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones with selected aryl and heteroaryl groups as the substituent have been synthesised as potential inhibitors of DNA-dependent protein kinase. A multiple-parallel approach, employing Suzuki cross-coupling methodology, was utilised in the preparation of 8-substituted 2-morpholin-4-yl-quinolin-4-ones. For this purpose 8-bromo-2-morpholin-4-yl-quinolin-4-one was required as an intermediate. This compound was obtained by adapting a literature route in which thermal cyclocondensation of (2-bromoanilino)-morpholin-4-yl-5-methylene-2,2-dimethyl[1,3]dioxane-4,6-dione afforded 8-bromo-2-morpholin-4-yl-quinolin-4-one. A multiple-parallel approach, employing Suzuki cross-coupling methodology, was also utilised to prepare 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones using 9-hydroxy-2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-one O-trifluoromethanesulfonate as an intermediate. 8-Substituted 2-morpholin-4-yl-quinolin-4-ones and 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones were both inhibitors of DNA-dependent protein kinase. When the substituent was dibenzothiophen-4-yl, dibenzofuran-4-yl or biphen-3-yl, IC50 values in the low nanomolar range were observed. Interestingly, the pyridopyrimidinones and quinolinones were essentially equipotent with the corresponding 8-substituted 2-morpholin-4-yl-chromen-4-ones previously reported (I. R. Hardcastle, X. Cockcroft, N. J. Curtin, M. Desage El-Murr, J. J. J. Leahy, M. Stockley, B. T. Golding, L. Rigoreau, C. Richardson, G. C. M. Smith and R. J. Griffin, J. Med. Chem., 2005, 48, 7829-7846). 相似文献
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