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1.
S. V. Volkov A. N. Levov A. T. Soldatenkov N. M. Kolyadina O. E. Volkova V. N. Khrustalev 《Chemistry of Heterocyclic Compounds》2007,43(9):1181-1188
The 4-nitro derivatives and an oxidation by-product, 9-hydroxy-2-methyl-3-oxo-9-phenyl-2,3-dihydro-9H-indeno[2,1-c]pyridine
were obtained by the nitration of N-alkyl-9-phenyl-2,3-dihydro-1H-indeno-[2,1-c]pyridines with sodium nitrite in acetic acid.
Their molecular structures were studied by X-ray structural analysis. The product of [2+3] cycloaddition, 5-methyl-3,7-diphenyl-3a,
4,5,6-tetrahydroindeno[2,1-c]isoxazolo[5,4-d]pyridine, was obtained by the interaction of 2-chloro-1-hydroxy-2-phenylazomethine
with 2-methyl-9-phenyl-2,3-dihydro-1H-indeno[2,1-c]pyridine.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1390–1399, September, 2007. 相似文献
2.
B. V. Lichitsky S. V. Shorunov A. O. Osipov A. N. Komogortsev A. A. Dudinov M. M. Krayushkin 《Russian Chemical Bulletin》2017,66(5):886-890
Previously unknown 6-acetyl-10-aryl-5-hydroxy-4-methyl-9,10-dihydropyrano[2,3-f]-chromene-2,8-diones were synthesized by multicomponent condensation of 6-acetyl-5,7-dihydroxy-4-methylchromen-2-one, aromatic aldehydes, and Meldrum´s acid. A fundamen-tal possibility of interconversion of substituted 6-acetyl-10-aryl-5-hydroxy-4-methyl-9,10-dihydropyrano[2,3-f]chromene-2,8-diones and methyl 3-(6-acetyl-5,7-dihydroxy-4-meth-yl-2-oxo-2H-chromen-8-yl)-3-arylpropionates was demonstrated. 相似文献
3.
N. S. Prostakov A. T. Soldatenkov M. V. Bagdadi O. S. Brindkha V. I. Kuznetsov V. A. Rezakov A. A. Fomichev 《Chemistry of Heterocyclic Compounds》1984,20(10):1128-1132
The fusion of 3,8-diphenyl-, 1,2-diphenyl-, and 6-methyl-2,7-diphenyl-indolizines with sulfur results in the formation of bis(indolizin-3-yl) disulfides with the respective substituents. Bis(2,8-diphenylindolizin-3-yl) disulfide is reduced to the original indolizine, and its treatment with nitric acid gives 2,8-diphenyl-1, 3-dinitroindolizine. Bis(dibenzo[b,g]indolizin-11-yl) disulfide is obtained from dibenzo[b,g]indolizine. The formation of the disulfides is apparently a general region of indolizines without substituents at C3 or C1 of the pyrrole ring. The structures of the disulfides obtained have been confirmed by data from x-ray diffraction analysis and NMR spectroscopy.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1371–1375, October, 1984. 相似文献
4.
D. S. Yufit Yu. T. Struchkov N. S. Prostakov V. I. Kuznetsov 《Chemistry of Heterocyclic Compounds》1986,22(8):844-848
An x-ray crystallographic investigation was made of 6-methyl-2,7-diphenyl-1,3-diformylindolizine, obtained by the formylation of 6-methyl-2,7-diphenylindolizine. The effect of various carbonyl-containing substituents at positions 1 and 3 on the geometry of the indolizine ring in the structually investigated indolizine derivatives is discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1048–1051, August, 1986. 相似文献
5.
1,2-Diaminopyridinium iodide underwent reaction with ethyl acetoacetate to form 1,4-dihydro-2-methyl-4-oxopyrido[1,2-a]pyrimidin-1-ium iodide, and with acetyl acetone it gave 2,4-dimethylpyrido[1,2-a]pyrimidin-5-ium iodide. Though 2-acetylcyclohexanone gave the corresponding 5-methyl-1,2,3,4-tetrahydropyrido[1,2-a]quinazolin-11-ium iodide, no reaction was observed with 2,6-dimethyl-3,5-heptanedione, 1-benzoylacetone, 1,3-diphenyl-1,3-propanedione and its p-methoxyphenyl derivative. However, 1-aminopyridinium iodide and acetyl acetone in the presence of base gave 3-acetyl-2-methylpyrazolo[1,5-a]pyridine and 1-amino-2-methylpyridinium iodide yielded the corresponding 3-acetyl-2,7-dimethylpyrazolo[1,5-a]pyridine. With ethyl acetoacetate, the latter salt formed 3-ethoxycarbonyl-2,7-dimethylpyrazolo[1,5-a]pyridine but with 2,6-dimethyl substituents in the pyridine ring no condensation occurred. Reaction of 1-amino-2-methylpyridinium iodide with benzaldehyde gave N-benzalimino-2-methylpyridinium iodide which, on treatment with base, resulted in the formation of 2-picoline and benzonitrile, providing a convenient method of deamination. 相似文献
6.
Irradiation (λ = 350 nm) of newly synthesized 2-acetyl- or 2-methyl-2-(alk-2-enyl)furan-3(2H)-ones 1 and 2-acetyl- or 2-methyl-2-(prop-2-enyl)thiophen-3(2H)-ones 2 affords the corresponding 1-acetyl- or 1-methyl-substituted 7-oxa- and 7-thiatricyclo[3.2.1.03,6]octan-2-ones 10 and 11 , respectively, via regioselective intramolecular [2 + 2] photocycloaddition in 65–95% yield (Scheme 2). The 1-acetyl-substituted O-derivatives 10b and 10c undergo ring opening on treatment with MeONa in MeOH at–78° to afford stereoselectively methyl 3-exo-acetyl-2-oxabicyclo[3.2.0]heptane-7-endo-carboxylates 12b and 12c , respectively, while a 2:1 diastereoisomeric mixture of methyl 3-acetyl-2-thiabicyclo[3.2.0]heptane-7-endo-carboxylates 13 and 14 is obtained from the corresponding S-derivative 11b . The outcome of the Huang-Minlon reduction of the 1-methyl-substituted ketones 10a and 11a is again influenced by the heteroatom in the tricycle. While 1-methyl-7-oxatricyclo[3.2.1.03,6]-octane ( 15 ) is the only product from the corresponding oxatricyclooctanone 10a , a 1:2 mixture of 1-methyl-7-thiatricyclo[3.2.1.03,6]-octane ( 16 ) and 3-methylbicyclo[3.1.1]hept-2-ene-6-endo-thiol ( 17 ) is obtained from the analogous S-compound 11a , both products stemming from a common carbanion precursor. 相似文献
7.
Reactions of 6-Amino-5-Cyano-3-Methyl-1,4-Diphenyl-1H 4H-Pyrano[2,3-C]Pyrazole and its Methanimidate
Reaction of 6-amino-5-cyano-3-methyl-1,4-diphenyl- 1H,4H-pyrano[2,3-c]pyrazole 1 with triethyl orthoformate in acetic anhydride gave its methanimidate 2, which reacts with primary aliphatic and aromatic amines to give 4,6-dihydro-3-methyl-1,4-diphenyl-6- (alkyl)pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidine-5(lH)- imine 3 and the starting compound 1 , respectively. Treatment of 1 with o-aminophenol gave 5-(2-benzoxalyl)- 1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazol- 6-amine 9. 相似文献
8.
Lyle W. Castle Yoshinori Tominaga Raymond N. Castle 《Journal of heterocyclic chemistry》1995,32(3):1033-1038
The 1H and 13C nmr spectral assignment of indolizino[3,4,5-a,b]isoindole and 2-methylthiobenz[f]-imidazo[5,1,2-c,d]indolizine are described. A concerted interpretation of the HMQC, HMQC-TOCSY, HMBC and nOe-difference experiments were used to assign the 1H and 13C resonances of indolizino-[3,4,5-a,b]isoindole, whereas for 2-methylthiobenz[f]imidazo[5,1,2-c,d]indolizine a concerted interpretation of the COSY, HMQC and HMBC experiments were used to generate spectral assignments. 相似文献
9.
V. E. Romanov E. E. Shul’ts M. M. Shakirov G. A. Tolstikov 《Russian Journal of Organic Chemistry》2011,47(4):581-588
Methyl 2-acetylamino-5-[2-(6-methylpyridin-3-yl)vinyl]benzoate reacted with phenacyl bromide to produce quaternary 1-(2-aryl-2-oxoethyl)-2-methyl-5-(4-acetylamino-3-methoxycarbonyl)pyridinium
bromides. 1,3-Dipolar cycloaddition of the latter to methyl propynoate and dimethyl but-2-ynedioate gave the corresponding
indolizine derivatives containing an anthranilic acid ester moiety. Reactions of acetylenes with N-phenacylpyridinium salts obtained from a diterpene alkaloid derivative, 2-(pyridin-3-yl)vinyl-substituted lappaconitine afforded
analogous compounds in which the indolizine fragment is conjugated to the aromatic ring of the alkaloid. 1,3-Dipolar cycloaddition
of 1-(2-aryl-2-oxoethyl)-2-methyl-5-(4-acetylamino-3-methoxycarbonyl) pyridinium bromides with methyl propynoate was regioselective. 相似文献
10.
Zhi-Hong Li Zhong-Tian Jin Bing-Zhu Yin Kimiaki Imafuku 《Journal of heterocyclic chemistry》1987,24(3):779-783
3-Acetyltropolone ( 1 ) reacted with bromine, iodine, and nitric acid to afford respectively 3-acetyl-5,7-di-bromotropolone ( 2 ), 3-acetyl-7-iodotropolone ( 3 ), and 3-acetyl-5-nitro- ( 4 ) and 3-acetyl-5,7-dinitrotropolone ( 5 ). Azo-coupling reactions of 1 gave 3-acetyl-5-arylazotropolones 7a-f. The Schmidt reactions of 2 and 3 gave respectively 5,7-dibromo- ( 9 ) and 7-iodo-2-methyl-8H-cyclohept[d]oxazol-8-one ( 10 ), while 4 gave 3-acetamido-5-nitrotropolone ( 11 ). Compounds 2 and 4 reacted with hydroxylamine to give 3-methyl-8H-cyclohept[d]isoxazol-8-ones 12 and 13. The reactions of 2 , 3 , and 4 with hydrazine gave 3-methyl-1,8-dihydrocycloheptapyrazol-8-ones 15 , 16 , and 17. 相似文献
11.
A new and convenient procedure for the synthesis of 1,6-naphthyridin-2(1H)-ones and their derivatives is described. In the first scheme 5-acetyl-6-[2-(dimethylamino)ethenyl]-1,2-dihydro-2-oxo-3-pyridinecarbonitrile ( 4 ) obtained by the reaction of N,N-dimethylformamide dimethyl acetal with 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile ( 3 ) was cyclized to 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile ( 5 ) by the action of ammonium acetate. Thermal decarboxylation of acid 7 obtained from the hydrolysis of nitrile 5 led to a mixture of 5-methyl-1,6-naphthyridin-2(1H)-one ( 8 ) and its dimer 9 . Hydrazide 11 obtained from nitrile 5 in two steps was converted to 3-amino-5-methyl-1,6-naphthyridin-2(1H)-one ( 12 ) by the Curtius rearrangement. The amino group of 12 was readily replaced by treatment with aqueous sodium hydroxide to yield 3-hydroxy-5-methyl-1,6-naphthyridin-2(1H)-one ( 13 ). In the second scheme, Michael reaction of enamines of type 20 with methyl propiolate, followed by ring closure gave 5-acyl(aroyl)-6-methyl-2(1H)-pyridinones ( 21 ) which in turn were treated with Bredereck's reagent to produce 5-acyl(aroyl)-6-[2-(dimethylamino)ethenyl]-2(1H)-pyridinones ( 22 ). Treatment of 22 with ammonium acetate led to the formation of 1,6-naphthyridin-2(1H)-ones 23 . 相似文献
12.
George Bobowski 《Journal of heterocyclic chemistry》1987,24(2):473-479
Treatment of 2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-1-methylcyclohexanol ( 2a ) with acetic anhydride or methyl isocyanate gave 2-acetyl-2,3,4,9-tetrahydro-1-(6-oxoheptylidene)-1H-pyrido[3,4-b]indole ( 3 ) or 1,3,4,9-tetrahydro-N-methyl-1-(6-oxoheptylidene)-2H-pyrido[3,4-b]indole-2-carboxamide ( 4 ), respectively. Simpler analogues, 1-alkyl-4,9-dihydro-3H-pyrido[3,4-b]indoles, 7 , subjected to identical reaction conditions, gave 2-acetyl-1-alkylidene-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles 8 and 1,3,4,9-tetrahydro-N-methyl-1-alkyli-dene-2H-pyrido[3,4-b]indole-2-carboxamides 9 , respectively. A limited lanthanide shift reagent study to determine stereochemical assignments was also performed. 相似文献
13.
N. S. Prostakov L. A. Gaivoronskaya Rogiros Anastasi Kamara Maiha Sarata Mohomon A. A. Savina 《Chemistry of Heterocyclic Compounds》1979,15(6):647-651
Indolizines, indeno[1,2-g]indolizine, and indeno[1,2-e]indolizine containing benzoyl and carbomethoxy groups in the five-membered ring were obtained, respectively, by condensation of ring-substituted N-phenacylpyridinium bromide and the analogous 3-methyl-2-azafluorenium bromide quaternary salts, as well as 4-azafluorenium bromide, with dimethyl acetylenedicarboxylate in the presence of triethylamine. A substituted indeno[2,3-f]indolizine was obtained from the analogous quaternary 9-oxo-3-methyl-2-azafluorenium quaternary salt by the Chichibabin method. 9-Oxo-3-methyl-2-azafluorenium dibenzoylmethylid and 5-oxo-2-phenyl-3-benzoylindeno[2,3-f]indolizine were also synthesized. Deuterium exchange in 9-oxo-3-methyl-2-phenacyl-2-azafluorenium bromide was studied by means of PMR spectroscopy, and information regarding the protonation of the substituted indeno[2,3-f]indolizines was obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 794–798, June, 1979. 相似文献
14.
Paul Gilgen Barry Jackson Hans-Jürgen Hansen Heinz Heimgartner Hans Schmid 《Helvetica chimica acta》1974,57(8):2634-2643
2, 3-Diphenyl-2H-azirine ( 1 ) reacts on irradiation with light of wavelength 290–350 nm with 1,4-benzoquinones 3–6 or with 1,4-naphthoquinones 7–9 forming the yellow to red coloured 1,3-diphenyl-2H-isoindole-4, 7-diones 10–13 (33–43% yield) resp. 1, 3-diphenyl-2H-benzo[f]isoindole-4,9-diones 14–16 (33–36% yield) (Scheme 1). The structures of these hitherto unknown products follow from the analytical and spectral data. The probable formation of the isoindole-diones is depicted in Scheme 2. The intermediate benzonitrile-benzylide ( 2 ), which most certainly arises, adds onto the unsubstituted C, C-double bond of the quinones and not onto the C,O-double bonds. On exclusion of atmospheric oxygen there results from 1 and 2-methyl-1, 4-benzoquinone ( 4 ) a product (probably b ) which hardly absorbs in the region 350–450 nm. The latter, with the agency of atmospheric oxygen (but not 4 ), is converted into 5-methyl-1, 3-diphenyl-2H-isoindole-4, 7-dione ( 11 ). The relative slowness of this oxidation (see Fig. 2) enables an almost complete photochemical transformation of the azirine 1 , which only weakly absorbs above 290 nm. Otherwise 11 , which strongly absorbs above 290 nm, would hinder the photolysis of 1 . 相似文献
15.
Yasunori Sudoh Zhong-Tian Jin Kimiaki Imafuku Hisashi Matsumura 《Journal of heterocyclic chemistry》1982,19(3):525-528
The reaction of 3-acetyltropolone ( 1 ) with hydroxylamine under the acidic condition gave 3-methyl-8H-cyclohept[d]isoxazol-8-one ( 4 ) and its oxime ( 5 ), and under the neutral condition gave 4 and 3-acetyltropolone oxime ( 6 ). The reaction of 3-acetyl-2-methoxytropone ( 2a ) with hydroxylamine under the acidic condition gave 4, 5 , and 4-methyl-1H-2,3-benzoxazin-1-one ( 7 ), and under the neutral condition gave 4, 7 , 3-methyl-8H-cyclohept[c]isoxazol-8-one ( 8 ), and its oxime ( 9 ). The reaction of 7-acetyl-2-methoxytropone ( 2b ) with hydroxylamine under the acidic condition gave 4 and 5 , and under the neutral condition gave 5, 7 , and 9 . 相似文献
16.
Alkylation of 3-methoxycarbonyl-2-methyl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine and 12-oxo-12,13-dihydro-7H-7azaindeno[1,2-b]phenanthrene using methyl iodide or allyl bromide in DMF solution in the presence of NaH occurs with high selectivity and
gives the corresponding C-alkyl derivatives in high yield. The acid cleavage of the 4a-alkylated 3-methoxycarbonyl-2-methyl-5-oxo-4a,5-dihydroindeno[1,2-b]pyridines has been studied.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 415–420, March, 2009. 相似文献
17.
Tetsuya Aono Jost H. Bieri Manfred Hesse Kalina Kostova Annalaura Lorenzi-Riatsch Yoshihiko Nakashita Roland Prewo 《Helvetica chimica acta》1985,68(4):1033-1053
Crystal structures have been determined of methyl trans-1-hydroxy-6-nitro-3-oxobicyclo[4.4.0]decane-2-carboxylate ( 19 ), cis-3-methyl-6-nitro-2-oxabicyclo[4.4.0]decan-1-ol ( 2 ), cis-7-hydroxy-1-nitrobicyclo[5.4.0]undecan-9-one ( 13 ), and the medium-ring compounds 2-acetyl-4-nitrocyclooctanone ( 9 ), methyl 5-nitro-2-oxocyclooctane-carboxylate ( 4 ), 2-acetyl-4-nitrocyclononanone ( 11 ), 2-acetyl-4-nitrocyclodecanone ( 15 ), benzyl 5-nitro-2,11-dioxocycloundecanecarboxylate ( 24 ), methyl 5-nitro-2,12-dioxocyclododecanecarboxylate ( 21 ), and 8-nitro-11-oxo-13-tridecanolide ( 7 ), which are intermediates, side products, or end products of the ‘Zip’ ring-enlargement reaction. The conformations of most of the medium-ring compounds are very similar to equal-sized ring compounds previously determine by other authors. 相似文献
18.
2-(Acetoacetamido)pyridine, 1 , and its 5-methyl derivative, 2 , with phosgene, gave 3-acetyl-2-chloro-4H-pyrido[1,2-a]pyrimidin- 4 -one, 5 , and 3-acetyl-2-chloro-7-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one, 6 , respectively. The structures of these compounds followed from their elemental analyses, and interpretations of their uv, ir, pmr, and X-ray spectra. An alternative route to 5 and 6 , which sought first to react 1 and 2 with methyl - and benzyl chloroformates, was unsuccessful, and led, instead, to elimination of the acetoacetyl group with concomitant formation of the carbamate derivatives, 10 and 11 . 相似文献
19.
J. Ignacio Andrés Rosario Herranz M. Teresa García López 《Journal of heterocyclic chemistry》1984,21(4):1221-1224
The synthesis of 6-methyl-7-(β-D-ribofuranosyl)imidazo[4,5-d]-v-triazin-4-one (8-methyl-2-azainosine ( 2) ) and 6-methyl-7-(β-D-glucopyranosyl)imidazo[4,5-d]-v-triazin-4-one ( 5 ) by diazotization of 5-amino-1-(β-D-ribofuranosyl)-2-methylimidazole-4-carboxamide ( 1 ) and diazotization of 5-amino-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-methylimidazole-4-carboxamide ( 3 ), followed by deacetylation of the resulting compound 4 , is described. The preparation of 6-methyl-5-(β-D-ribofuranosyl)imidazo[4,5-d]-v-triazin-4-one ( 10 ) and 6-methyl-5-(β-D-glucopyranosyl)imidazo[4,5-d]-v-triazin-4-one ( 11 ) by glycosylation of 6-methylimidazo[4,5-d]-v-triazin-4-one (8-methyl-2-azahypoxanthine, ( 7) ) is also described. Structural assignments were made on basis of analytical and 1H-nmr and uv spectral data. 相似文献
20.
A method for the preparation of novel oxaza and diaza polycyclic 9-oxa-4-azaphenanthrene, 5H-pyrido[2,3-a]pyrrolizine, 5H,6H-pyrido[3,2-g]indolizine, and 5H,6H-indeno[2,1-a]indole is described, based on tandem reactions: aza-Wittig reaction of N-vinylic phosphazenes with functionalized aldehydes and an intramolecular aza-Diels-Alder reaction. 相似文献