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1.
V. O. Koz’minykh V. I. Goncharov E. N. Koz’minykh 《Russian Journal of Organic Chemistry》2006,42(11):1715-1718
A simple preparative procedure was developed for 3-(2-oxoalkylidene)-3,4-dihydroquinoxalin-2(1H)-ones, 4,5-dihydroxy-1-[3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene]-3,5-octadiene-2,7-dione, and 3-(2,3-dihydroxy-4-methyl-5-oxo-1,3-cyclopentadien-1-yl)quinoxalin-2(1H)-one by reaction of methyl ketones first with diethyl oxalate in the presence of sodium, and then with o-phenylenediamine. 相似文献
2.
I. V. Mashevskaya I. G. Mokrushin K. S. Bozdyreva A. N. Maslivets 《Russian Journal of Organic Chemistry》2011,47(2):253-257
Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1Hpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones. 相似文献
3.
K. S. Bozdyreva Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2008,44(4):607-611
3-[(Z)-3,3-Dimethyl-2-oxobutylidene]-3,4-dihydroquinoxalin-2(1H)-one and its 1-phenyl-substituted analog reacted with oxalyl chloride to give the corresponding 3-pivaloylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones. Reactions of the latter with o-phenylenediamine led to the formation of 3,3′-(3,3-dimethyl-2-oxobutane-1,1-diyl)di[quinoxalin-2(1H)-ones].
Original Russian Text ? K.S. Bozdyreva, Z.G. Aliev, A.N. Maslivets. 2008, published in Zhurnal Organicheskoi Khimii, 2008,
Vol. 44, No. 4, pp. 612–616.
For communication LVI, see [1]. 相似文献
4.
A process for preparing 3-substituted 3,4-dihydroquinoxalin-2(1H)-ones is proposed. It is based on the reaction of o-phenylenediamine with amides, di- and mono-esters of maleic acid as well as (E)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)acrylic acid in the presence of N,N′-carbonyl-diimidazole. 相似文献
5.
A. S. Fokin Ya. V. Burgart V. I. Saloutin O. N. Chupakhin 《Russian Journal of Organic Chemistry》2005,41(9):1354-1358
3-Ethoxy- and 3-arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates undergo cyclization by the action of hydrazine hydrate and phenylhydrazine to give ethyl 4-pentafluorobenzoylpyrazole-5-carboxylates. The reaction of 3-ethoxymethylidene-2,4-dioxo-4-pentafluorophenylbutanoate with o-phenylene-diamine leads to formation of 3-[2-(2-aminophenylamino)-1-pentafluorobenzoylethenyl]-1,2-dihydroquinoxa-lin-2-one. 3-Arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates react with o-phenylenediamine to afford 3-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinolin-3-yl)-1,2-dihydroquinoxalin-2-ones and/or 3-(2-arylamino-1-pentafluorobenzoylethenyl)-1,2-dihydroquinoxalin-2-ones. 相似文献
6.
V. V. Bolotov S. N. Kovalenko S. V. Kovaleva V. I. Stepanenko 《Chemistry of Heterocyclic Compounds》2004,40(2):211-213
A method is presented for the synthesis of 3-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1,4-dihydroquinoxalin-2-one and 2-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2H-1,4-benzoxazin-3(4H)-one by the reaction of ethyl 2-oxoindoline-2-glyoxylate with o-aminophenol and o-phenylenediamine. Proposed reaction mechanisms are presented. 相似文献
7.
1-Methyl-3,4-dihydroquinoxalin-2(1H)-one was heated with a range of aldehydes to generate intermediate azomethine ylides which underwent [3 + 2] cycloaddition reactions with N-methyl or N-phenylmaleimide to give substituted tetrahydropyrroloquinoxalinones. Only one (racemic) stereoisomer was formed in each case and the stereochemical outcome was verified by single crystal X-ray analysis. The products from this multicomponent reaction could be oxidised with DDQ to the pyrroloquinoxalinones. 相似文献
8.
3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones reacted with 1,3,3-trimethyl-2-methylidene-2,3-dihydro-1H-indole (Fischer’s base) to give (2Z)-1-aryl-2-[3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene]-5-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)pentane-1,3,4-triones. 相似文献
9.
4-Acetyl- and 4-succinyl-3-(2-aryl-2-oxoethyl)-3,4-dihydroquinoxalin-2(1H)-ones undergo the rearrangement into (Z)-2-(3-arylquinoxalin-2-ylidene)acetic acids accompanied by the elimination of the acyl groups. The nitration of 3-(2-oxo-2-phenylethyl)-3,4-dihydro-quinoxalin-2(1H)-one affords 5-nitro- and 7-nitro-2-carboxymethylidenequinoxalines. The bromination of quinoxalin-2-ones in AcOH gives 3-aryl-2-carboxymethylidenequinoxalines
and the corresponding 7-bromo derivatives, with the former products predominating. 相似文献
10.
《中国化学快报》2021,32(11):3627-3631
Herein, a rapid alkenylation of quinoxalin-2(1H)-ones enabled by a combination of Mannich-type reaction and solar photocatalysis is demonstrated. A wide range of functional groups are compatible, affording the corresponding products in moderate-to-good yields. Control experiments illustrate that the in situ generated 1O2 plays a central role in this reaction. This green and efficient strategy provides a practical solution for the synthesis of potentially bioactive compounds that containing a 3,4-dihydroquinoxalin-2(1H)-one structure. 相似文献
11.
I. V. Mashevskaya I. G. Mokrushin L. V. Kuslina Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2011,47(3):417-420
Recyclization of 3-aroyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones by the action of benzoic acid hydrazides gave N-[2,4-dihydroxy-5-oxo-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)-2-aryl-2,5-dihydro-1H-pyrrol-1-yl]benzamides whose structure was proved by X-ray analysis. 相似文献
12.
Mamedov V. A. Kalinin A. A. Gubaidullin A. T. Rizvanov I. Kh. Chernova A. V. Doroshkina G. M. Litvinov I. A. Levin Ya. A. 《Russian Journal of Organic Chemistry》2003,39(1):131-140
3-Benzoyl-1,2-dihydroquinoxalin-2-one reacts with hydrazine and thiosemicarbazide to give the corresponding hydrazone and thiosemicarbazone. The reaction with arylhydrazines yields 3-(-arylazobenzylidene)-1,2,3,4-tetrahydroquinoxalin-2-ones which are tautomeric to the respective arylhydrazones. On heating in boiling acetic acid, the products of both types undergo intramolecular cyclocondensation with formation of 3-phenylpyrazolo[3,4-b]quinoxalines (3-phenylflavazoles). 3-Benzoyl-1,2-dihydroquinoxalin-2-one thiosemicarbazone gives rise to flavazole structure only in the presence of methyl 3-chloro-2-oxo-3-phenylpropionate as a trap of thiocarbamoyl moiety. The cyclization of 3-(-hydrazonobenzyl)-1,2-dihydroquinoxalin-2-one is accompanied by formation of quinoxalyl ketone azine. 相似文献
13.
(Z)-3-(α-Alkoxycarbonyl-α-cyanomethylene)-2-oxo-1,2,3,4-tetrahydroquinoxalines 3 and (Z)-3-(α-alkoxycarbonyl-α-cyanomethylene)-3,4-dihydrobenzo[g]quinoxalin-2(1H)-ones 5 possessing various alkoxycarbonyl groups were prepared in good yields directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates 1 with o-phenylenediamine ( 2 ) or with 2,3-diaminonaphthalene ( 4 ), respectively. Furthermore, 2,3-diaminopyridine ( 6 ) and 3,4-diaminopyridine ( 7 ) were reacted with the diethyl ester 1b to give (Z)-2-(α-cyano-α-ethoxycarbonylmethylene)-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one ( 8 ) and (Z)-3-(α-cyano-α-ethoxycarbonylmethylene)-3,4-dihydro-1H-pyrido[3,4-b]pyrazin-2-one ( 9 ), respectively. The structural studies of 3, 5, 8 , and 9 were carried out by nmr experiments in some details. 相似文献
14.
V. O. Koz’minykh V. I. Goncharov K. Sh. Lomidze E. N. Koz’minykh 《Russian Journal of Organic Chemistry》2007,43(1):64-67
2-(2-Oxo-2,3-dihydro-1H-indol-3-ylidene)acetic acid esters reacted with benzene-1,2-diamine or 2-aminobenzenethiol to give (2-oxo-2,3-dihydro-1H-indol-3-yl)-substituted 3,4-dihydroquinoxalin-2(1H)-ones or 2H-1,4-benzothiazin-3(4H)-ones. 相似文献
15.
Krishna C. Joshi Anshu Dandia Sangeeta Sanan 《Journal of heterocyclic chemistry》1989,26(5):1397-1400
The reaction of 3-(2-oxocycloalkylidene)indol-2-one 1 with thiourea and urea derivatives has been investigated. Reaction of 1 with thiourea and urea in ethanolic potassium hydroxide media leads to the formation of spiro-2-indolinones 2a-f in 40–50% yield and a novel tetracyclic ring system 4,5-cycloalkyl-1,3-diazepino-[4,5-b]indole-2-thione/one 3a-f in 30–35% yield. 3-(2-Oxocyclopentylidene)indol-2-one afforded 5′,6′-cyclopenta-2′-thioxo/ oxospiro[3H-indole-3,4′(3′H)pyrimidin]-2(1H)-ones 2a,b and 3-(2-oxocyclohexylidene)indol-2-one gave 2′,4′a,5′,6′,7′,8′- hexahydro-2′-thioxo/oxospiro[3H-indole-3,4′ (3′H)-quinazolin]-2(1H)-ones 2c-f . Under exactly similar conditions, reaction of 1 with fluorinated phenylthiourea/cyclohexylthiourea/phenylurea gave exclusively spiro products 2g-1 in 60–75% yield. The products have been characterized by elemental analyses, ir pmr. 19F nmr and mass spectral studies. 相似文献
16.
Robert Y. Ning George F. Field Leo H. Sternbach 《Journal of heterocyclic chemistry》1970,7(3):475-478
The cyclic nitrones 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide ( 5a ) and 1,3-dihydro-7-methylthio-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide ( 5b ) are photoisomerized to readily isolable oxaziridines, 7-chloro-4,5-epoxy-5-phenyl-1,3,4–5-tetrahydro-2H-1,4-benzodiazepin-2-one ( 6a ) and 4,5-epoxy-5-phenyl-1,3,4,5-tetrahydro-7-methylthio-2H-1,4-benzo-diazepin-2-one ( 6b ). Oxaziridine 6b upon further irradiation gave ring expansion and ring contraction products, 4,6-dihydro-2-phenyl-9-methylthio-5H-1,3,6-benzoxadiazocin-5-one ( 7b ) and 4-benzoyl-3,4-dihydro-6-methylthioquinoxalin-2(1H)-one ( 8b ) respectively. The ring contraction product, 4-benzoyl-6-chloro-3,4-dihydroquinoxalin-2(1H)-one ( 8a ), was obtained from irradiation of oxaziridine 6a . 相似文献
17.
K. S. Bozdyreva I. V. Smirnova A. N. Maslivets 《Russian Journal of Organic Chemistry》2005,41(7):1081-1088
(Z)-3-Phenacylidene- and (Z)-3-hetaroylmethylidene-1-phenyl-1,2,3,4-tetrahydroquinoxalin-2-ones react with oxalyl chloride to give 3-acyl-5-phenyl-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-1,2,4-triones. Thermolysis of the latter generates acyl(3-oxo-4-phenyl-3,4-dihydroquinoxalin-2-yl)ketenes which are stabilized via [4 + 2]-cyclodimerization followed by [1,3]-acylotropic shift to afford 4-acyl-3-acyloxy-2-(3-oxo-4-phenyl-3,4-dihydroquinoxalin-2-yl)-6-phenyl-5,6-dihydro-1H-pyrido[1,2-a]quinoxaline-1,5-diones.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 1101–1108.Original Russian Text Copyright © 2005 by Bozdyreva, Smirnova, Maslivets. 相似文献
18.
Norton P. Peet Shyam Sunder Robert J. Barbuch Michael R. Whalon John C. Huffman 《Journal of heterocyclic chemistry》1988,25(2):543-547
The reaction of 2-hydrazinobenzothiazole (1) with ethyl acetoacetate has twice been reported to yield a fused triazepinobenzothiazolone, namely, 3-methyl[1,2,4]triazepino[3,4-b]benzothiazol-5(4H)-one (4). We have repeated this work and reassigned the reaction product as 2-(2-benzothiazolyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one (5) on the basis of X-ray crystallography. 相似文献
19.
Valeria M. Zakharova Ortwin Brede Mikhail A. Kuznetsov Joachim Sieler 《Tetrahedron》2010,66(1):379-384
A number of N,N′-linked benzoannelated isothiazol-3(2H)-one 1,1-dioxides, not available via oxidation of isothiazolium salts, were obtained with good yields by reaction of N-amino heterocycles with 2-chlorosulfonylbenzoyl chloride and evaluated for their inhibitory activity toward human leukocyte elastase (HLE) and acetylcholinesterase (AChE). 2-(Phthalimid-1-yl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide and 2-(2-methyl-4-oxo-3(4H)-quinazolinyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide were found to be inhibitors of HLE and tested as potential precursors of nitrogen-centered radicals using 266 nm laser flash photolysis. 相似文献
20.
Gold-catalyzed isomerization of 2-alkynyl-1-tetralones afforded the corresponding 2-naphthylmethyl ketones in good to high yields. For example, the reaction of 2-{4-(methoxyphenyl)methyl}-2-(phenylethynyl)-3,4-dihydronaphthalen-1(2H)-one and 2-benzyl-2-(phenylethynyl)-3,4-dihydronaphthalen-1(2H)-one in the presence of 5 mol % of (Ph3P)AuCl and 5 mol % of AgOTf in THF at 50 °C gave 2-{1-(4-methoxyphenylmethyl)naphthalen-2-yl}-1-(4-methoxyphenyl)ethanone and 2-(1-benzylnaphthalen-2-yl)-1-phenylethanone in 85% and 96% yields, respectively. The present reaction proceeds through [1,2] alkyl migration followed by oxygen transfer. 相似文献