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1.
V. I. Shvedov V. K. Vasil'eva O. B. Romanova A. N. Grinev 《Chemistry of Heterocyclic Compounds》1973,9(8):951-952
The nitration of 3-ethoxycarbonyl-4-hydroxy-2-methyl- and 4-chloro-3-ethoxycarbonyl-2-methylthiophenes has given the corresponding 5-nitro derivatives of thiophene. The 4-chloro-3-ethoxycarbonyl-2-methylthiophene was synthesized by the decarboxylation of 3-chloro-4-ethoxycarbonyl-5-methylthiophene-2-carboxylic acid, which is formed by the oxidation of 3-chloro-4-ethoxycarbonyl-5-methylthiophene-2-carbaldehyde.For Communication IV, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1024–1025, August, 1973. 相似文献
2.
Ho Sik Kim Yoshihisa Kurasawa Chiemi Yoshii Minako Masuyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1990,27(4):1115-1117
The reaction of the 2-substituted 6-chloroquinoxaline 4-oxides 1a or 1b with 2-fold molar amount of methyl propiolate resulted in the 1,3-dipolar cycloaddition reaction to give 8-chloro-1,3-bismethoxycarbonyl-4-(piperidin-1-yl)pyrrolo[1,2-a]quinoxaline 4a or 8-chloro-1,3-bismethoxycarbonyl-4-(morpholin-4-yl)pyrrolo-[1,2-a]quinoxaline 4b , respectively. Compound 4a or 4b was transformed into 8-chloro-3-methoxycarbonyl-4-(piperidin-1-yl)pyrrolo[1,2-a]quinoxaline 5a or 8-chloro-3-methoxycarbonyl-4-(morpholin-4-yl)pyrrolo[1,2-a]-quinoxaline 5b , respectively. The structure of 4a,b was confirmed by the NOE measurement among the C1 -H , C 2-H and C 9-H proton signals of 5a,b . An additional reaction mechanism was proposed for the ring transformation of isoxazolo[2,3-a]quinoxalines into pyrrolo[1,2-a]quinoxalines. 相似文献
3.
Yoshihisa Kurasawa Aiko Ishikura Kazue Ikeda Tomoyoshi Hosaka Yuko Matsumoto Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1994,31(1):233-238
The reaction of 7-chloro-4-ethoxycarbonylmethylene-4,5-dihydro-1,2,4-triazolo[4,3-a]quinoxaline 6 with 4-ethoxycarbonyl-1-methyl-1H-pyrazole-5-diazonium chloride or 4-cyano-1,3-dimethyl-1H-pyrazole-5-diazonium chloride gave 7-chloro-4-[α-(4-ethoxycarbonyl-1-methyl-1H-pyrazol-5-ylhydrazono)-ethoxycarbonylmethyl]-1,2,4-triazolo[4,3-a]quinoxaline 8a or 7-chloro-4-[α-(4-cyano-1,3-dimethyl-1H-pyrazol-5-ylhydrazono)ethoxycarbonylmethyl]-1,2,4-triazolo[4,3-a]quinoxaline 8b , respectively, while the reaction of 7-chloro-4-ethoxycarbonylmethylene-4,5-dihydrotetrazolo[1,5-a]quinoxaline 7 with 4-ethoxycarbonyl-1-methyl-1H-pyrazole-5-diazonium chloride or 4-cyano-1,3-dimethyl-1H-pyrazole-5-diazomum chloride provided 7-chloro-4-[α-(4-ethoxycarbonyl-1-methyl-1H-pyrazol-5-ylhydrazono)ethoxycarbonylmethyl]tetrazolo[1,5-a]quinoxaline 9a or 7-chloro-4-[α-(4-cyano-1,3-dimethyl-1H-pyrazol-5-ylhydrazono)ethoxycarbonylmethyl]tetrazolo[1,5-a]quinoxaline 9b , respectively. Compounds 8a,b and 9a,b showed the tautomeric equilibria between the hydrazone imine C and diazenyl enamine D forms in dimethyl sulfoxide and/or trifluoroacetic acid, and the effects of solvent and temperature on the tautomer ratios of C to D were studied by the nmr measurements in a series of mixed trifluoroacetic acid/dimethyl sulfoxide media (compounds 8a,b and 9a,b ) and at various temperatures (compounds 8a,b ). 相似文献
4.
In contrast with earlier literature data [7], both acrylic esters and acrylonitrile underwent Michael addition to l-methyl-3,4-dihydroisoquinolines 1-4 to yield the diesters 5-9 or the dinitrile 10 , respectively. Compounds 5-10 were converted by Claisen condensation to 1-[(3′-methoxycarbonyl- or 1-[(3′-ethoxycarbonyl-4′-oxo)-l'-cyclohexyl]-3,4-dihydroisoquinoline derivatives 11-16 . Several derivatives of 12 were prepared. The new compounds possess various pharmacological actions. 相似文献
5.
2-Substituted 8-cyano-6-ethoxycarbonyl-3-hydroxy-5-methylimidazo[1,2-a]pyridine was formed from the interaction of 2-chloro-5-ethoxycarbonyl-6-methylnicotinonitrile with -amino acids in DMF. The same nitrile on boiling with anthranilic acid or its esters in butanol gave, respectively, 2-(2-carboxyanilino)- or 2-(2-alkoxycarbonylanilino)-5-ethoxycarbonyl-6-methylnicotinonitriles which cyclized on heating in PPA to give 9-alkoxycarbonyl(or 9-carboxy)-3-ethoxycarbonyl-2-methyl-10H-benzo[b]-1,8-naphthyridin-5-ones. 相似文献
6.
-[2-(5-Methoxycarbonyl)furyl]-2,4-dihydroxy- and 2,4,6-trihydroxyacetophenones were obtained by the condensation of polyphenols with (2-methoxycarbonyl-5-furyl)acetonitrile. 7-Acetoxy- and 5,7-diacetoxy-2-methyl-3-[2-(5-methoxycarbonyl)furyl]chromones were obtained from them by reaction with acetic anhydride in the presence of triethylamine and were subsequently deacylated to 7-hydroxy and 5,7-dihydroxy compounds. 7-Hydroxy- and 5,7-dihydroxy-2-ethoxycarbonyl-3-[2-(5-methoxycarbonyl)furyl]chromones were obtained from the indicated acetophenones by reaction with ethoxalyl chloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1317–1320, October, 1972. 相似文献
7.
Y Kita M Kirihara M Sasho Y Fujii J Sekihachi R Okunaka Y Tamura K Shimooka 《Chemical & pharmaceutical bulletin》1990,38(3):585-589
The 4-methoxy-5-methylpyrano[4,3-b]indole-1,3(4H,5H)-dione (9), prepared from methyl 3-methoxycarbonyl-1-methylindol-2-yl acetate (6), underwent a strong base-induced cycloaddition reaction with 2-chloro-6,6-ethylenedioxy-5,6,7,8-tetrahydro-1,4-naphthoquinone (11) to give the tetrahydronaphtho[2,3-b]carbazole-7,12-dione (10), regioselectively. The cycloadduct (10) was successfully converted to a D-ring indole analogue of daunomycin (1a). 相似文献
8.
In the reactions of the recently synthesized β-ketoesters 1-[(3′-methoxycarbonyl- and 1-[(3′-ethoxycarbonyl-4′-oxo)-1′-cyclohexyl]-3,4-dihydroisoquinoline 4, 5 with amidines or cyclic guanidines, a number of 2-substituted-6-(6′,7′-dimethoxy-3′,4′-dihydro-1′-isoquinolyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one derivatives 6–8 were prepared. The new compounds possess various pharmacological actions. 相似文献
9.
I. V. Ukrainets V. V. Kravtsova A. A. Tkach G. Sim 《Chemistry of Heterocyclic Compounds》2008,44(2):173-177
Treatment of 1R-4-chloro-3-ethoxycarbonyl-2-oxo-1,2-dihydroquinolines with p-toluenesulfonylhydrazide in refluxing ethanol
and in the presence of triethylamine gives the 3-hydroxy-5R-1,5-dihydropyrazolo[4,3-c]quinolin-4-ones. The possible mechanism
of formation, features of the steric structure of the synthesized compounds, and their NMR and mass spectra are discussed.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 233–238, February, 2008. 相似文献
10.
Yoshihisa Kurasawa Atsushi Satoh Satoyuki Ninomiya Harumi Arai Kiyoko Arai Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(4):1229-1231
The reaction of the quinoxaline 1 with 4-ethoxycarbonyl-1H-pyrazole-5-diazonium chloride 7 at room temperature gave 3-[α-(4-ethoxycarbonyl-1H-pyrazol-5-ylhydrazono)methoxycarbonylmethyl]-2-oxo-1,2-dihydroquinoxaline 8. The pmr spectrum of 8 in deuteriodimethylsulfoxide supported the presence of two tautomers 8-I and 8-II. Refluxing of 8 in N,N-dimethylformamide or acetic acid resulted in cyclization to afford 8-ethoxycarbonyl-4-oxo-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine 9. Compound 9 was also obtained directly by the reaction of 1 with 7 under reflux in better yield. The reaction of 9 with hydrazine hydrate provided the hydrazinium salt 10 , while the reactions of 9 with triethyl and trimethyl orthoformates in the presence of 1,8-diazabicyclo[5,4,0]-7-undecene produced 8-ethoxycarbonyl-4-ethoxyl-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)pyrazolo[5,1-c][1,2,4]triazine 11a and 8-ethoxycarbonyl-4-methoxyl-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)pyrazolo[5,1-c][1,2,4]triazine 11b , respectively. The chlorination of 11a with phosphoryl chloride gave 3-(3-chloroquinoxalin-2-yl)-8-ethoxycarbonyl-4-ethoxylpyrazolo[5,1-c]-[1,2,4]triazine 12 , whose reaction with morpholine afforded 8-ethoxycarbonyl-4-ethoxyl-3-[3-(morpholin-4-yl)-quinoxalin-2-yl]pyrazolo[5,1-c][1,2,4]triazine 13. 相似文献
11.
Oxidation of aldehyde 4-chloro-2,3,5,6-tetrafluorophenylhydrazones (1) with [bis(acetoxy)iodo]benzene leads to the formation of nitrile imines (2) which reacted in situ with ethyl acrylate to produce 3-substituted-1-(4-chloro-2,3,5,6-tetrafluorophenyl)-5-ethoxycarbonyl-4,5-dihydropyrazoles (3) in moderate to good yields. The structures of new compounds were fully confirmed by their spectral data, elemental analyses and X-ray diffraction (XRD) analysis. A plausible reaction mechanism for the synthesis of title compounds is presented. 相似文献
12.
Maria Rosaria Del Giudice Franco Gatta Guido Settimj 《Journal of heterocyclic chemistry》1990,27(4):967-973
Oxidation of 1-methyl-3-methoxycarbonyl-β-carboline with selenium dioxide gave 1-formyl-3-methoxycarbonyl-β-carboline II . Compound II reacted with acetic or propionic anhydride to give easily the 2-methoxycarbonyl-6H-indolo[3,2,1-d,e][1,5]naphthyridin-6-ones III ; reaction of II with some primary amines led to the formation of the Schiff bases IV , which were reduced to the 1-aminomethyl-3-methoxycarbonyl-β-carbolines V with sodium borohydride. Cyclization of V with aqueous formaldehyde led to the pyrimido[3,4,5-lm]pyrido[3,4-b]indoles VI . Analogously, cyclization with formaldehyde, acetone or 1,1′-carbonyldiimidazole of the 3-aminomethyl- 1,2,3,4-tetrahydro-β-carbolines VIII , obtained by reaction of 3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline VII with amines followed by lithium aluminium hydride reduction of the resulting amides, gave the imidazo[1′,5′-1,6]pyrido[3,4-b]indoles IX and X . Dieckmann cyclization of 3-methoxycarbonyl-2-[(3-ethoxycarbonyl)-1-propyl]-1,2,3,4-tetrahydro-β-carboline XI led to a 1:1 mixture of the β-ketoesters XII and XIII , which underwent deethoxycarbonylation to 5,6,8,9,10,11,11a,12-octahydroindolo[3,2-b]quinolizin-11-one XIV . Finally, the polyphosphoric acid (or esters) catalyzed cyclization of the N-acyl derivatives XVI of 3-hydrazinocarbonyl-β-carboline XV led smoothly to the 3-(1,3,4-oxadiazol-2-yl)-β-carbolines XVII . 相似文献
13.
The desmotropy of differently substituted (R∗)-3-ethoxycarbonyl-2-aryl-3,5-dihydro-4,1-benzothiazepines and 3-ethoxycarbonyl-2-aryl-1,5-dihydro-4,1-benzothiazepines was investigated. The target 4,1-benzothiazepines were obtained via the ring transformation of (2R∗,2aS∗)-2-chloro-2a-aryl-2,2a-dihydro-2H,4H-azeto[1,2-a][3,1]benzothiazin-1-ones with sodium ethoxide in ethanol. The β-amino ester intermediate of the ring-enlargement reaction was isolated. Surprisingly, the desmotropes obtained could be separated by column chromatography and proved to be unexpectedly stable in solution. Further comparative studies revealed the existence of only the enamine forms of regioisomeric 2-ethoxycarbonyl-3-aryl-4,5-dihydro-7,8-dimethoxy-1,4-benzothiazepine derivatives; in this case, no desmotropy occurred. The structures were proved by means of NMR and IR spectroscopy. 相似文献
14.
Continuing our investigation of the properties of 2-methyl-3-ethoxycarbonyl-4-hydroxythiophene (I) [1], we found that it readily undergoes electrophilic substitution reactions. We studied the behavior of I under the conditions of the Vilsmeier reaction. The structures of the reaction products depend on the temperature conditions: at 30–35°C, 2-methyl-3-ethoxycarbonyl-4-hydroxy-5-formylthiophene (H) is formed in 74% yield while 2-methyl-3-ethoxycarbonyl-4-chloro-5-formylthiophene (III) is formed in 50% yield at 100°. The reaction of I with dimethylbenzamide and phosphorus oxychloride gives 2-methyl-3-ethoxycarbonyl-4-hydroxy-5-benzoylthiophene (IV) in 41% yield.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, p. 427, March, 1972. 相似文献
15.
Guido Settimj Maria Rosaria Del Giudice Rosella Ferretti Franco Gatta 《Journal of heterocyclic chemistry》1988,25(5):1391-1397
Condensation of diethyl formylamino- or diethyl acetylaminomalonate with 4-, 5- or 6-nitrogramine 1 afforded the diethyl formylamino- or the diethyl acetylamino[(nitroindol)-3-ylmethyl]malonates 2 ; reduction of the nitro group followed by N-formylation or acetylation of the resulting amino compounds 3 , led to the 4-, 5-and 6-acylamino derivatives 4 . Cyclization of 4 in the presence of polyphosphoric esters gave the 3,3-bis(ethoxycarbonyl)-3,4-dihydro-β-carbolines 5 , which underwent lithium chloride/water catalyzed monodeethoxycarbonylation to the corresponding 5-, 6- and 7-acylamino-3-ethoxycarbonyl-β-carbolines 6 , whose acidic hydrolysis led finally to the 5-, 6- and 7-amino-3-ethoxycarbonyl-β-carbolines 9 . The 6-amino compounds 9b-e were obtained also by direct nitration of 3-methoxycarbonyl-β-carboline 7a and of 3-ethoxycarbonyl-β-carboline 7c , followed by the nitro group reduction of the resulting nitro carbolines 8 . Preliminary studies of the binding to rabbit brain benzodiazepine receptor sites indicate compounds 9b and 9c to inhibit the 3H-diazepam binding at 10?8 M concentrations. 相似文献
16.
Yoshihisa Kurasawa Megumi Kanoh Yumiko Kamigaki Mari Okiyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(3):1015-1018
The reactions of the pyrazole-5-diazonium salt 3 with malononitrile and ethyl cyanoacetate gave 4-amino-3-cyano-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazine 7 and 4-amino-3,8-bisethoxycarbonylpyrazolo[5,1-c]-[1,2,4]triazine 8 , whose reactions with p-chloroaniline hydrochloride afforded 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)amidinopyrazolo[5,1-c][1,2,4]triazine 9 and 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)car-bamoylpyrazolo[5,1-c][1,2,4]triazine 10 , respectively. The reactions of 7 and 8 with o-phenylenediamine di-hydrochloride provided 9-ethoxycarbonyl-13H-spiro[benzimidazole-2′(3′H),6(5H)-pyrazolo[1,5′:3,4][1,2,4]tri-azino[5,6-b][1,5]benzodiazepine] hydrochloride 11a and 9-ethoxycarbonyl-6-oxo-13H-5,6-dihydropyrazolo-[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepine 12 , respectively. The antifungal activity of the above compounds was described. 相似文献
17.
Condensation of methyl 2-isoxazolin-5-on-3-yl acetate ( 3 ) and 3-(N,N-dimethylamino)-2-ethoxycarbonylacrolein ( 6 ) gave 5-ethoxycarbonyl-7-methoxycarbonyl-2,1-benzisoxazolin-3-one ( 7a ). Simple hydrolysis of the diester 7a afforded 5,7-dicarboxy-2,1-benzisoxazolin-3-one ( 7b ). 相似文献
18.
V. Ya. Vorob'eva E. E. Mikhlina K. F. Turchin L. N. Yakhontov 《Chemistry of Heterocyclic Compounds》1983,19(7):782-785
The reduction of 2-ethoxycarbonyl-3-oxoquinuclidine oxime hydrochloride leads to 2-ethoxycarbonyl-3-amino-2,3-dehydroquinuclidine, from which pyrimido[5,4-b]quinuclidine derivatives were obtained by reaction with formamide, methyl isocyanate, and phenyl isothiocyanate. It is shown that 7-hydroxypyrazolo[4,3-b]quinuclidine is formed in the reaction of 2-ethoxycarbonyl-3-acetamido-2,3-dehydroquinuclidine with hydrazine hydrate.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 971–974, July, 1983. 相似文献
19.
Keitaro Senga Misuzu Ichiba Hashime Kanazawa Sadao Nishigaki 《Journal of heterocyclic chemistry》1982,19(1):77-80
Synthesis and properties of hitherto unknown thiazolo[5,4-d]pyrimidine 1-oxides are described. For example, the reaction of 6-chloro-1,3-dimethyl-5-nitrouracil (I) with methyl thioglycolate in the presence of excess triethylamine afforded 2-methoxycarbonyl-4,6-dimethylthiazolo[5,4-d]pyrimidine-5,7-(4H,6H)dione 1-oxide (IIIa), which is a versatile intermediate for the preparation of various thiazolo[5,4-d]pyrimidine derivatives. 相似文献
20.
A. N. Grinev I. A. Kharizomenova M. V. Kapustina Yu. N. Sheinker L. M. Alekseeva N. M. Rubtsov 《Chemistry of Heterocyclic Compounds》1987,23(4):384-386
Bromination of 2-acylamino-3-ethoxycarbonyl-7-oxo-4,5,6,7-tetrahydrobenzo[b]-thiophenes has been studied. This reaction affords 2-acylamino-6,6-dibromo-3-ethoxycarbonyl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene, which on dehydrobro-mination gives 6-bromo-7-oxybenzo[b]thiophene derivatives. The 4,6-dibromo- and 4,6-dinitro-7-oxybenzo[b]thiophenes were also obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 460–462, April, 1987. 相似文献