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1.
V. L. Savel'ev O. S. Artamonova A. V. Makarov V. S. Troitskaya A. V. Antonova V. G. Vinokurov 《Chemistry of Heterocyclic Compounds》1989,25(9):1011-1014
The reaction of 3-nitro-4-chlorocoumarin with anthranilic acid was used to synthesize N-(3-nitro-4-coumarinyl)-anthranilic acid, from which, through the acid chloride, we obtained a number of amides, which were reduced to N-(3-amino-4-coumarinyl)anthranilic acid amides The latter are cyclized under the influence of hydrochloric acid to 6,7,8,13-tetrahydro[1]benzopyrano-[4,3-b][1, 4]benzodiazepine-6,8-dione, which was also obtained from N-(3-amino-4-coumarinyl)anthranilic acid by its thermolysis or treatment with hydrochloric acid.See [1] for our preliminary communication.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1208–1212, September, 1989. 相似文献
2.
The direction of the reaction of anthranilic acids with o-bromomethylphenylacetonitrile upon fusion depends on the temperature
and nature of the substituent in the anthranilic acid. The reaction may lead to three types of products: Derivatives of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones
below 150°C and to 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one or derivatives of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones
above 150°C depending on the nature of the substituent in the anthranilic acid. A study was carried out on the mechanism for
the formation of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones, which permitted the preparation
of 6-(4-methylphenyl)-6,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1059–1067, July, 2007. 相似文献
3.
Maria C. Aversa Placido Giannetto Giuseppe Bruno 《Journal of heterocyclic chemistry》1988,25(1):297-299
Four representatives of the new ring system [3,1]benzoxazino[2,1-b][1,3]benzoxazine, as determined by X-ray crystallography, were prepared by reaction of N-(2-hydroxybenzyl)anthranilic acids with trifluoroacetic anhydride. 相似文献
4.
10-Alkylamino-2-methy1-1,2,3,4-tetrahydrobenzo[b]-1,6-naphthyridines were obtained by cyclization of alkylamides of N-(1-methyl-4-piperidylidene)anthranilic acids and also by reaction of 10-chloro-2-methyl-1,2,3,4-tetrahydrobenzo-[b]-1,6-naphthyridines with amine hydrochlorides.See [1] for communication VI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 263–265, February, 1976. 相似文献
5.
P. P. Mukovoz A. V. Gorbunova V. O. Koz’minykh P. A. Slepukhin I. N. Ganebnykh O. S. El’tsov E. N. Koz’minykh 《Russian Journal of Organic Chemistry》2016,52(7):993-999
Methyl 3,4-dihydroxy-6-oxoalka-2,4-dienoates reacted with anthranilic acid hydrazide to give methyl [5-alkyl-1-(2-aminobenzamido)-2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrol-2-yl]acetates. The reaction of anthranilic acid hydrazide with ethyl 3,4-dihydroxy-6-oxohepta-2,4-dienoate afforded ethyl (2Z)-(3a-hydroxy-2-methyl-10-oxo-3,3a,5,10-tetrahydro-4H-pyrazolo[5,1-c][1,4]benzodiazepin-4-ylidene)acetate as solvate with one methanol molecule. The structure of the isolated compounds was determined on the basis of IR and NMR spectra and X-ray diffraction data. 相似文献
6.
Ryo Mizunuma Teruhiko Tanaka Yoshihiro Nakamura Yuki Kamijima Yoshio Kabe 《Tetrahedron》2018,74(5):544-548
Recent reports describe the different products resulting from the reaction of C60 with benzyne generated from anthranilic acid derivatives and isoamyl nitrate in the presence and absence of triethylamine. Reinvestigation here via 1H, 13C, HMBC NMR and Mass spectroscopy elucidates that these products are the [6,6] closed C60-fused δ lactones, and not the [5,6] open fulleroids which would result from benzyne addition. Furthermore, theoretical calculations show that the open isomer [5,6] benzyne addition is less stable than the [5,6] closed isomer as an isolable product. 相似文献
7.
L. A. Shemchuk V. P. Chernykh P. S. Arzumanov I. L. Starchikova 《Russian Journal of Organic Chemistry》2007,43(12):1830-1835
Treatment of anthranilic acid hydrazide with 2 equiv of ethoxalyl chloride gave the corresponding diester which underwent cyclization in acetic anhydride to produce ethyl 3-(ethoxalylamino)-4-oxo-3,4-dihydroquinazoline-2-carboxylate. Acylation of anthranilic acid hydrazide first with succinic anhydride and then with ethoxalyl chloride led to the formation of 4-[2-(2-{[ethoxy(oxo)acetyl]amino}benzoyl)hydrazino]-4-oxobutanoic acid whose cyclization in acetic acid afforded N-(2-ethoxycarbonyl-4-oxo-3,4-dihydroquinazolin-3-yl)succinamic acid, while in acetic anhydride ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate was obtained. The latter was brought into reactions with amines and hydrazine hydrate and alkaline hydrolysis. Acylation of 2-[2-(2-aminobenzoyl)hydrazinocarbonyl]benzoic acid with ethoxalyl chloride gave ethyl N-[2-(phthalimidocarbamoyl)phenyl]oxamate, and with succinic anhydride, 3-[4-oxo-3-phthalimido-3,4-dihydroquinazolin-2-yl]propionic acid. 4-[2-(2-Aminobenzoyl)hydrazino]-4-oxobutanoic acid reacted with phthalic anhydride in boiling acetic acid to give phthalazino[1,2-b]quinazoline-5,8-dione via elimination of succinic acid residue. 相似文献
8.
Yu. M. Volovenko E. V. Resnyanskaya A. V. Tverdokhlebov 《Chemistry of Heterocyclic Compounds》2002,38(3):324-330
A convenient method has been developed for the synthesis of 3-hetaryl-1,2,4,5-tetrahydropyrrolo[1,2-a]quinazoline-2,5-diones by the interaction of 4-chloro-2-hetaryl-3-oxobutyronitriles with substituted anthranilic acids. 相似文献
9.
L. A. Shemchuk V. P. Chernykh O. S. Krys’kiv 《Russian Journal of Organic Chemistry》2008,44(7):1006-1008
In the reaction with cyclic anhydrides the anthranilic acid 2-N-phenylhydrazide depending on conditions yielded either anthranilic acid 2-N-acyl-2-N′-phenylhydrazides, 2-R-3-anilinoquinazolin-4(3H)-ones, or derivatives of 1-phenylpyridazino[3,2-b]quinazoline-2,10-dione. 相似文献
10.
Gustav Zigeuner Klaus Schweiger Monika Baier 《Monatshefte für Chemie / Chemical Monthly》1981,112(3):335-340
The reaction of1,1-dimethyl-3-oxobutylisothiocyanate1 with methyl anthranilate takes place via the 2-(2-thioxopyrimidine-1)-benzoic methylester2 a, which is rearranged to the methyl thioxopyridineanthranilate3 a. 3 a is alkylated by methyl anthranilate to the corresponding methylthio-product4 a, which reacts with anthranilic acid via5a to the benzo [1,6]naphthyridino[5,6-b]-chinazoline6. 6 can also be synthesized by condensation of 2-methylthiopyridines9 a, b with anthranilic acid and 4-dimethylaminpyridine-2-thione8a with methyl anthranilate resp. 相似文献
11.
4-Arylamino-6-methyl-5,6,7,8-tetrahydro-2,3-benzo-1,6-naphthyridines are obtained from N-(1-methyl-4-piperidylidene)anthranilic acid arylamides.See [1] for communication I.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1393–1395, October, 1973. 相似文献
12.
A. M. Sh. El-Sharief F. F. Mahmoud N. M. Taha E. M. Ahmed 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):573-589
Abstract N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)cyanothioformamide was synthesized from the corresponding 4-amino-pyrazole. Various cyanothioformamides were reacted with different arylidenes of cyanothioacetamide to produce either 4-imino-5-thioxo-3-(pyrroline & pyrrolidine)carbonitrile or pyrrolo[3,2-d]thiazole. Interaction of thiohydantoin with the arylidenes of either malononitrile or cyanothioacetamide furnished the same 5-aminothiopyrano[2,3-d]-imidazole-6-carbonitriles. Also, thiohydantoin reacted with the anilide of chloroacetic acid and with anthranilic acid to produce thieno[2,3-d]-imidazole-2-one and imidazo[4,5-b]quinoline-2,9-dione, respectively. 相似文献
13.
L. M. Potikha 《Chemistry of Heterocyclic Compounds》2007,43(6):759-768
The reaction of 3-haloanthranilic acids with o-bromomethylphenylacetonitrile gave 2-(2-carboxy-6-halophenyl)-1,4-dihydro-3(2H)-isoquinolinium
bromides. 2-Chlorophenylisoquinolinium bromides are readily converted into 4-R-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones
by heating >145°C, but 2,4-dibromophenylisoquinolinium bromide only on fusing with anthranilic acid. The effect of the nature
and position of substituents in the quinazoline fragment of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones on the rate of
the rearrangement into 6,11-dihydro-13H-isoquino[3,2-b]quinazol-13-ones has been studied. The oxidation and borohydride reduction
of 6,11-dihydro-13H-isoquino[3,2-b]quinazol-13-ones has been studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, 899–909, June, 2007. 相似文献
14.
F. M. Avotin'sh M. V. Petrova A. Ya. Strakov 《Chemistry of Heterocyclic Compounds》2001,37(10):1241-1243
The corresponding diamides have been synthesized by the interaction of the diacid chlorides of cis-2,2-dimethyl-3-carboxycyclobutaneacetic acid (pinic acid) and cis-2,2-dimethylcyclobutane-1,3-diacetic acid (sym-homopinic acid) with two equivalents of anthranilic acid. Treatment of the diamides with formamide gave 2,2-dimethyl-1-[4(3H)-quinazolinon-2-yl]methyl-3-[4(3H)-quinazolinon-2-yl]cyclobutane and 2,2-dimethyl-1,3-di[4(3H)-quinazolinon-2-ylmethyl]cyclobutane respectively. 相似文献
15.
Unusual expulsions of [H2O + CO2] from the M+˙ of N-(o-carboxyphenyl)anthranilic acid, [H2O + CH2O] from the M+˙ of N-(o-methoxyphenyl)anthranilic acid and [H2O + ˙NO2] from the M+˙ of N-(o-nitrophenyl) anthranilic acid were observed under electron impact conditions. These processes are stepwise in the corresponding para-substituted N-phenylanthranilic acids. The proposed fragmentation pathways and their mechanisms are supported by B/E linked-scan spectra, collision-activated decomposition (CAD)–mass-analysed ion kinetic energy (MIKE) spectra, high-resolution data, deuterium labelling and chemical substitution. 相似文献
16.
The first total synthesis of naturally occurring (Z)-11-(2-oxopropylidene)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(10H)-one,a unique cycloanthranilylproline derivative, has been achieved from readily available anthranilic acid in five steps. 相似文献
17.
Dong Han Kim 《Journal of heterocyclic chemistry》1981,18(4):855-856
The treatment of N-(2-hydroxyphenyl)anthranilic acids with cyanogen bromide in the presence of triethylamine gave dibenz[b,e][1,4]oxazepin-11-(5H)ones in good yields. 相似文献
18.
[reaction: see text] The synthesis of phenyl-substituted 8,9-dibromofluoranthene and p-dodecylphenyl-substituted 8,9-fluoranthene anthranilic acid is presented. Their synthetic potential as 8,9-didehydrofluoranthene precursors is demonstrated in combination with a new biscyclopentadienone by the synthesis of novel phenyl-substituted PAHs with up to 14 annulated rings. The crystal structure of 7,16-diphenylfluorantheno[8,9-k]fluoranthene is given. 相似文献
19.
François-René Alexandre Amaya BerecibarRoger Wrigglesworth Thierry Besson 《Tetrahedron》2003,59(9):1413-1419
Efficient microwave-assisted multi-step synthesis of 8H-quinazolino[4,3-b]quinazolin-8-one was investigated. The synthesis involved two Niementowski condensations from anthranilic acids. Homogeneous or heterogeneous conditions were studied with the aim to develop convenient syntheses of the desired compounds. 相似文献
20.
Ahmad S. Shawali Abdou O. Abdelhamid Hamdi M. Hassaneen Abdelfattah Shetta 《Journal of heterocyclic chemistry》1982,19(1):73-75
Diazotized anthranilic acid and its methyl ester react with substituted phenacyl thiocyanates 3 to give in both cases the corresponding thiadiazolo[2,3-b]quinazolines 7a-e . A mechanism is proposed and it is substantiated by alternate synthesis of 7a from the hydrazidoyl chlorides 9a,b and potassium thiocyanate. 相似文献