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1.
Issa Yavari Loghman Moradi Farough Nasiri Hoorieh Djahaniani 《Monatshefte für Chemie / Chemical Monthly》2005,36(9):1757-1761
The regioselective reaction of N1-benzyl-N2-(4-nitrophenyl)ethanediamide with dialkyl acetylenedicarboxylates or alkyl propiolates in the presence of triphenylphosphine
leads to dialkyl 4-benzylamino-1-(4-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates or alkyl 4-benzylamino-1-(4-nitrophenyl)-2-oxo-5-pyrrolidinecarboxylates in good yields. 相似文献
2.
The Common 2′ -deoxypyrimidine and -purine nucleosides, thymidine ( 4 ), O4-[2-(4-nitrophenyl)ethyl]-thymidine ( 17 ), 2′-deoxy-N4-[2-(4-nitrophenyl)ethoxycarbonyl]cytidine ( 26 ), 2′-deoxy-N6-[2-(4-nitrophenyl)-ethoxycarbonyl]adenosine- 39 , and 2′-deoxy-N2-[2-(4-nitrophenyl)(ethoxycarbonyl]-O6-[2–4-nitrophenyl)ethyl]-guanosine ( 52 ) were further protected by the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) and the 2-(2,4-dinitrophenyl)ethoxycarbonyl (dnpeoc) group at the OH functions of the sugar moiety to form new partially and fully blocked intermediates for nucleoside and nucleotide syntheses. The corresponding 5′-O-monomethoxytrityl derivatives 5 , 18 , 30 , 40 , and 56 were also used as starting material to synthesize some other intermediates which were not obtained by direct acylations. In the ribonucleoside series, the 5′ -O-monomethoxytrityl derivatives 14 , 36 , 49 , and 63 reacted with 2-(4-nitrophenyl) ethyl chloroformate ( 1 ) to the corresponding 2′,3′-bis-carbonates 15 , 37 , 50 , and 64 which were either detriylated to 16 , 38 , 51 , and 65 , respectively, or converted by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) treatment to the 2′,3′-cyclic carbonates 66 – 69 . The newly synthesized compounds were characterized by elemental analyses and UV and 1H-NMR spectra. 相似文献
3.
Holger Lang Margarete Gottlieb Michael Schwarz Silke Farkas BerndS. Schulz Frank Himmelsbach Ramamurthy Charubala Wolfgang Pfleiderer 《Helvetica chimica acta》1999,82(12):2172-2185
A series of new base-protected and 5′-O-(4-monomethoxytrityl)- or 5′-O-(4,4′-dimethoxytrityl)-substituted 3′-(2-cyanoethyl diisopropylphosphoramidites) and 3′-[2-(4-nitrophenyl)ethyl diisopropylphosphoramidites] 52 – 66 and 67 – 82 , respectively, are prepared as potential building blocks for oligonucleotide synthesis (see Scheme). Thus, 3′,5′-di-O-acyl- and N 2,3′-O,5′-O-triacyl-2′-deoxyguanosines can easily be converted into the corresponding O6-alkyl derivatives 6 , 8 , 10 , 12 , 14 , and 16 by a Mitsunobu reaction using the appropriate alcohol. Mild hydrolysis removes the acyl groups from the sugar moiety (→ 9 , 11 , 13 , 15 , and 19 (via 18 ), resp.) which can then be tritylated (→ 38 – 42 ) and phosphitylated (→ 57 – 61 ) in the usual manner. N 2-[2-(4-nitrophenyl)ethoxycarbonyl]-substituted and N 2-[2-(4-nitrophenyl)ethoxycarbonyl]-O6-[2-(4-nitrophenyl)ethyl]-substituted 2′-deoxyguanosines 5 and 7 , respectively, are synthesized as new starting materials for tritylation (→ 28 , 35 , and 37 ) and phosphitylation (→ 54 , 56 , 70 , and 78 ). Various O4-alkylthymidines (see 20 – 24 ) are also converted to their 5′-O-dimethoxytrityl derivatives (see 43 – 47) and the corresponding phosphoramidites (see 62 – 66 and 79 – 82 ). 相似文献
4.
Nurani S. Narasimhan Heinz Heimgartner Hans-Jürgen Hansen Hans Schmid 《Helvetica chimica acta》1973,56(4):1351-1370
Benzonitrile p-nitrobenzylide ( 5 ) undergoes 1,3-dipolar cyclo-additions in the presence of 3-phenyl-2H-azirines ( 1 ), yielding in benzene at 0° 2-(p-nitrophenyl)-4,5-diphenyl-1,3-diazabicyclo[3.1.0]hex-3-enes ( 7 , scheme 2). Under the basic conditions of the reaction mixture, 7 a and 7 b are partially converted to 2-(p-nitrophenyl)-4,5-diphenyl-1,6-dihydropyrimidines ( 8a, b ) which are dehydrogenated by oxygen to the corresponding pyrimidines 9a and 9b , respectively. 3-Phenyl-2H-azirines ( 1 ) form, on heating at 145° in xylene in the presence of the azalactone 32 (2,4-diphenyl-Δ2-oxazolin-5-one), 4-(aziridin-2′-yl)-2,4-diphenyl-Δ2-oxazolin-5-ones ( 33 , scheme 11). 33 arises from an ene reaction of the enol form of 32 with 1 . Similar ene reactions are observed with the azirines 1 and dimedone ( 37 , scheme 12). Under the ene reaction conditions (xylene, 145°), the non-isolated intermediate primary adducts ( 38a and 38b ) undergo rearrangements of the vinylcyclopane-cyclopentene type to give 6,6-dimethyl-4-oxo-1,3-diphenyl-4, 5, 6, 7-tetrahydroisoindole ( 40 ) and 6, 6-dimethyl-4-oxo-3-phenyl-4, 5, 6, 7-tetrahedroindole ( 42 ), respectively. 相似文献
5.
M. Madesclaire P. Coudert V. Gaumet V. P. Zaitsev Yu. V. Zaitseva 《Chemistry of Heterocyclic Compounds》2006,42(5):665-670
We have synthesized a series of (1R,2R,4S,5S,8S)-2,8-diaryl-4-(4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octanes as a result
of reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediol with aromatic aldehydes. The structure of the compounds obtained
was established on the basis of 1H NMR data.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 757–763, May, 2006. 相似文献
6.
Summary. The regioselective reaction of N1-benzyl-N2-(4-nitrophenyl)ethanediamide with dialkyl acetylenedicarboxylates or alkyl propiolates in the presence of triphenylphosphine
leads to dialkyl 4-benzylamino-1-(4-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates or alkyl 4-benzylamino-1-(4-nitrophenyl)-2-oxo-5-pyrrolidinecarboxylates in good yields. 相似文献
7.
Some 1-(2-furyl)-2-arylethylenes, where the furan nucleus is substituted in position 5 with a methyl or p-chlorophenyl group and where the aryl group is phenyl, p-nitrophenyl, α-naphthyl or β-naphthyl, have been prepared by the Perkin reaction and subsequent decarboxylation of the acid. The compounds 1-12 were prepared lor of photochemistry and photoelectron spectroscopy studies. Their geometrical configurations has been established by 1H nmr and ir spectra. 相似文献
8.
J. Couquelet M. Madesclaire F. Leal V. P. Zaitsev S. Kh. Sharipova 《Chemistry of Heterocyclic Compounds》2001,37(7):898-902
The reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediol with glutaraldehyde has been studied. It has been established on the basis of AM1 and PM3 calculations and 1H NMR spectra recorded in the presence of the shift reagent Eu(fod)3 that (1S,3S,4S,7R,11R)-3-(4-nitrophenyl)-11-aza-2,6-dioxatricyclo[5,3,1,04,11]undecane is formed as the result of the reaction. 相似文献
9.
M. Madesclaire V. P. Zaitsev J. V. Zaitseva S. Kh. Sharipova 《Chemistry of Heterocyclic Compounds》2007,43(10):1325-1332
A synthesis is reported for (4R,5R)-and (4S,5S)-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidin-2-ones and (1′R,4R)-and (1′S,4S)-4-[hydroxy(4-nitrophenyl)methyl]oxazolidin-2-ones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols. The effect of the experimental conditions on the formation of these compounds
was studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1562–1570, October, 2007. 相似文献
10.
Reduction of 1,2-Bis[(Z)-(2-nitrophenyl)-NNO-azoxy]benzene1: Synthesis of Cyclotrisazobenzene ( = (5E,6aZ,11E,12aZ,17E,18aZ)-5,6,11,12,17,18-Hexaazatribenzo[aei][1,3,5,7,9,11]cyclododeca-hexaene) Na2S reduction of 1,2-bis[(Z)-(2-nitrophenyl)-NNO-azoxy]benzene ( 2 ) yielded 3 deoxygenated products: the (known) red 2,2′-((E,E)-1,2-phenylenbisazo)dianiline ( 3 , 23%), the orange 2-[2-((E)-2-aminophenylazo)phenyl]-2H-benzotriazol ( 4 , 55%) and the colorless 2,2′-(1,2-phenylene)di-2H-benzotriazol ( 5 , 13%). The constitutions of 3 – 5 and of 6 , the N-acetyl derivative of 4 , were deduced from their 1H-NMR spectra (chemical shifts, couplings, and symmetry properties), and the configurations of 3 , 4 , and 6 at their N,N-double bonds are assumed to be the same as in 2 . Oxidation of 3 with 2 mol-equiv. of Pb(OAc)4 afforded 5 (47%) and a novel, highly symmetrical macrocycle, called cyclotrisazobenzene ( 7 , 24%). The constitution of 7 as a tribenzo-hexaaza[12]annulene and its (E)-configuration at the N,N-bonds was confirmed by X-ray analysis. The molecular symmetry expressed by the 1H-, 13C- and 15N-NMR spectra of 7 reveals a rapid torsional motion around the six N,C bonds. This implies that the N,N-double bonds in the cyclic 12π-electron system (or 24π-electron system if the benzene rings are included) of 7 are highly localized. 相似文献
11.
rac-threo-α-(2, 2-Dichloroacetamido)-β-hydroxy-p-nitrohydrocinnamaldehyde (3) and rac-erythro-α-(2, 2-dichloroacetamido)-β-hydroxy-p-nitrohydrocinnamaldehyde (4) were synthesized starting from α-acetamido-p-nitroacetophenone (7) , and their structures were proved bn? reduction to rac-chloramphenicol (19) and rac-erythro-2-(2, 2-dichloroacetamido)-1-(p-nitrophenyl)v 1, 3-propanediol (14) respectively. 3 exhibited only low antibacterial activity compared to rac-chloramphenicol (19) . 相似文献
12.
Vjacheslav Lapachev Svetlana Stekhova Vladimir Mamaev 《Monatshefte für Chemie / Chemical Monthly》1987,118(5):669-670
The tautomeric properties ofo-hydroxyphenylazines have been investigated by17O NMR and UV spectroscopy. 2-(o-Hydroxyphenyl)-pyridine and itsp-nitrophenole analog II exist in chloroform or ethanol as a phenol A. In the case of 2-(2-hydroxy-5-nitrophenyl)-quinoline the NH-tautomer is realized, the content of which increases when going to the dinitro-analog IV.
Die Tautomerie von 2-(o-Hydroxyphenyl)-azinen (Kurze Mitteilung)
Zusammenfassung Es wurden die tautomeren Eigenschaften vono-Hydroxyphenylazinen mittels17O-NMR und UV-Spektroskopie untersucht. 2-(o-Hydroxyphenyl)-pyridin und seinp-Nitrophenol-Analog II existieren in Chloroform und Ethanol als Phenol A. Das 2-(2-Hydroxy-5-nitrophenyl)-chinolin liegt als NH-Tautomer vor, dessen Anteil im Dinitro-Analog IV noch steigt.相似文献
13.
S. Munichandra Reddy D. Subba Rao K. Madhu Ch. Subramanyam P. Gnana Kumari 《Phosphorus, sulfur, and silicon and the related elements》2018,193(3):136-140
A series of new 2-(benzo[d]thiazol-2-yl) phenyl-4-nitrophenyl alkyl/aryl substituted phosphoramidate derivatives (7a-j) of biological interest are synthesized in two steps via an in situ process without the isolation of the intermediate. 2-(Benzo[d]thiazol-2-yl) phenol (3) was treated with 4-nitrophenyl phosphorodichloridate(4) to obtain the monochloro intermediate, 2-(benzo[d]thiazol-2-yl)phenyl (4-nitrophenyl) phosphorochloridate(5). It was subsequently reacted with various amines, 6(a-j) to afford the desired title products. IR, NMR (1H, 13C and 31P), mass spectral and elemental analysis are used to characterize the structures of the newly synthesized compounds. The antibacterial and antifungal activities are determined by the growth of inhibition of bacteria and fungi of the title compounds at two concentrations, 50 and 100 µg/mL, and minimum inhibitory concentrations to the active compounds. The compounds 7e, 7f and 7j exhibited promising inhibition activity against bacterial strains and 7c, 7e and 7i against A. niger and C. albicans and MIC values are in the range of 10.0–15.0 µg/mL. 相似文献
14.
The (2-dansylethoxy)carbonyl (= {2-{[5-(dimethylamino)naphthalen-l-yl]sulfonyl}ethoxy}carbonyl; dnseoc) group was employed for protection of the amino functions of the aglycone residues. The lactam function of 2′-deoxyguanosine was on the one hand unprotected and on the other hand alkylated at O6 of the aglycone with the 2-(4-nitrophenyl)ethyl (npe) and 2-(phenylsulfonyl)ethyl (pse) group, respectively. The syntheses of monomeric building blocks, both phosphoramidites and nucleoside- functionalized supports, are described for the three common 2′-deoxynucleosides (2′-deoxycytidine, 2′-deoxyadenosine, 2′-deoxyguanosine). As kinetic studies with the tritylated nucleosides showed, the dnseoc group is more labile towards DBU cleavage than the corresponding 2-(4-nitrophenyl)ethyl-(npe) and [2-(4-nitrophenyl)ethoxy]carbonyl(npeoc)-protected analogues (see Table 2). These results were confirmed by the very fast deprotection rate of the dnseoc groups at some oligonucleotides. 相似文献
15.
Simanenko Yu. S. Popov A. F. Karpichev E. A. Prokop'eva T. M. Savelova V. A. Bunton C. A. 《Russian Journal of Organic Chemistry》2002,38(9):1314-1325
1-Cetyl-3-(2-hydroxyiminopropyl)imidazolium chloride and bromide were synthesized for the first time. These compounds are functionalized zwitterionic surfactants which give rise to micelle formation in aqueous solution. Kinetic and thermodynamic analysis of nucleophilic cleavage of p-nitrophenyl p-toluenesulfonate, diethyl p-nitrophenyl phosphate, and ethyl p-nitrophenyl ethylphosphonate in the presence of 1-cetyl-3-(2-hydroxyiminopropyl)imidazolium halide micelles showed that the latter are powerful nucleophilic reagents whose kinetic behavior can be described in terms of a simple pseudophase distribution model. The efficiency of substrate solubilization with zwitterionic surfactant micelles and the reactivity of the oximate fragment in the micelle phase were estimated on a quantitative level. The observed acceleration of SN2 reactions with the examined p-nitrophenyl esters relative to analogous reactions of zwitterionic 1-methyl-3-(2-hydroxyiminopropyl)imidazolium halides is, respectively, 12800, 550, and 900 times; it is explained mainly by increased concentration of the reactants in micelles. 相似文献
16.
α-Substituted β-(5-nitro-2-furyl)ethynyls were conveniently prepared by the deamination of α-substituted β-(5-nitro-2-furyl)vinylamines. Also the application of this reaction toward α,β-bis(p-nitrophenyl)vinylamine was examined and afforded α,β-bis(p-nitrophenyl)ethynyl as the main product. 相似文献
17.
S. N. Dmitrieva M. V. Churakova N. A. Kurchavov A. I. Vedernikov L. G. Kuz’mina A. Ya. Freidzon A. A. Bagatur’yants Yu. A. Strelenko J. A. K. Howard S. P. Gromov 《Russian Chemical Bulletin》2010,59(6):1192-1206
A number of N-alkylnitrobenzoaza-15-crown-5 with the macrocycle N atom conjugated with the benzene ring were obtained. The structural and
complexing properties of these compounds were compared with those of model nitrobenzo- and N-(4-nitrophenyl)aza-15-crown-5 using X-ray diffraction, 1H NMR spectroscopy, and DFT calculations. The macrocyclic N atom of benzoazacrown ethers are characterized by a considerable
contribution of the sp3-hybridized state and a pronounced pyramidal geometry; the crownlike conformation of the macrocycle
is preorganized for cation binding, which facilitates complexation. The stability constants of the complexes of crown ethers
with the NH4
+, EtNH3
+, Na+, K+, Ca2+, and Ba2+ ions were determined by 1H NMR titration in MeCN-d3. The most stable complexes were obtained with alkaline-earth metal cations, which is due to the higher charge density at
these cations. The characteristics of the complexing ability of N-alkylnitrobenzoaza-15-crown-5 toward alkaline earth metal cations are comparable with analogous characteristics of nitrobenzo-15-crown-5
and are much better than those of N-(4-nitrophenyl)aza-15-crown-5. 相似文献
18.
E. V. Babaev K. Yu. Pasichnichenko V. B. Rybakov S. G. Zhukov A. V. Efimov 《Chemistry of Heterocyclic Compounds》2000,36(9):1086-1090
The reaction of 5-morpholino-2-(p-nitrophenyl)indolizine with dimethyl sulfate gives the sulfonation product - methyl 5-morpholyl-2-(p-nitrophenyl)indolizine-1-sulfonate. Its structure was proved by X-ray crystallographic analysis. 相似文献
19.
Dietrich Dpp Mohsen Abdel-Motaal Gomaa Gerald Henkel Ahmed Mokhtar Nour El-Din 《Journal of heterocyclic chemistry》1995,32(2):603-610
Nucleophilic attack by N2 of N1 N2-diarylformamides 1a-c on C-2 of chloranil (2) and subsequently by N1 on C-1 of 2 initiates the formation of benzimidazolinones 8a-c. In contrast, when 1b-e is reacted with 2,3-dichloro-1,4-naphthoquinone (9) , both chlorine atoms are successively substituted by the two nitrogen atoms and 2-(arylamino)-3-(N-formylarylamino)-1,4-naphthoquinones 13b-e result, which (probably via their cyclic tautomers 12b-e ) may be cyclodehydrogenated to form N1,N3-diarylnaphtho[2,3-d] imidazoline-2,4,9-triones (as 14b,c ). On the other hand, N1,N2diarylacetamidines 15a-d attack 2 and 9 at C-2 with N2 but subsequently exert nucleophilic character at the acetamidine α-carbon attacking C-1 of 2 and 9 , respectively, thus forming 1-aryl-2-(arylimino)-3a-hydroxy-2,3,3a,6-tetrahydro-1N-indol-6-ones 18a-d and 3-aryl-2-(arylimino)-9b-hydroxy-2,3,5,9b-tetrahydro-1-H-benz[e]indol-5-ones 19b,c , respectively. The latter may be thermally dehydrated to the fully conjugated 2,5-dihydro-3H-benz[e]indol-5-ones 20b,c. Unambiguous structural assignments for 18b and 20c are made on the basis of X-ray crystal structure analyses. 相似文献
20.
U. Siemeling T. Türk U. Hammermeister 《Monatshefte für Chemie / Chemical Monthly》1995,126(6-7):725-732
Summary 2-(2-Nitrophenyl)-ethanol (2) was methylated with dimethyl sulfate to give 2-(2-methoxyethyl)-1-nitrobenzene (3a) which then was reduced with hydrazine hydrate in the presence ofRaney nickel to 2-(2-methoxyethyl)-aniline (1a). Compound1a can be transformed into the N-monosilylated derivative4 by lithiation withn-butyllithium and subsequent reaction with chlorotrimethylsilane. Reaction of2 withp-toluenesulfonyl chloride yields 2-(2-nitrophenyl)-ethylp-toluenesulfonate (5), which reacts with sodium thiomethoxide to give 2-(2-nitrophenyl)-ethylp-toluenesulfonate (5), which reacts with sodium thiomethoxide to give 2-(2-thiomethoxyethyl)-1-nitrobenzene (3b).3b was reduced with hydrazine hydrate in the presence ofRaney nickel to yield 2-(2-thiomethoxyethyl)-aniline (1b). Ethyl (2-nitrophenyl)-acetate (6) could be dimethylated with methyl iodide in the presence of potassiumtert-butoxide and 18-crown-6 to give ethyl 2-methyl-2-(2-nitrophenyl)-propionate (7). Reduction of7 with lithium borohydride yields 2,3-dihydro-3,3-dimethyl-1H-indole (9) and 2-[(1-hydroxy-2-methyl)-2-propyl]-aniline (10).
Synthese von 2-(2-Methoxyethyl)- und 2-(2-Thiomethoxyethyl)-anilin und verwandten Verbindungen
Zusammenfassung 2-(2-Nitrophenyl)-ethanol (2) wurde mit Dimethylsulfat zu 2-(2-Methoxyethyl)-1-nitrobenzol (3a) methyliert, das sich mit Hydrazinhydrat in Gegenwart vonRaney-Nickel zu 2-(2-Methoxyethyl)-anilin (1a) reduzieren läßt. Verbindung1a kann durch Metallierung mitn-Butyllithium und anschließende Reaktion mit Chlortrimethylsilan in dasN-monosilylierte Derivat4 umgewandelt werden. Reaktion von2 mitp-Toluolsulfonylchlorid ergab 2-(2-Nitrophenyl)-ethyl-p-Toluolsulfonat (5), das mit Natriumthiomethanolat zu 1-Nitro-2-(2-thiomethoxyethyl)-benzol (3b) reagiert.3b wurde mit Hydrazinhydrat in Gegenwart vonRaney-Nickel zu 2-(2-Thiomethoxyethyl)-anilin (1b) reduziert. Ethyl-2-(nitrophenyl)-acetat (6) kann mit Methyliodid in Gegenwart von Kalium-tert-butoxid und 18-Krone-6 zu Ethyl-2-methyl-2-(2-nitrophenyl)-propionat (7) dimethyliert werden. Reduktion von7 mit Lithiumborhydrid lieferte 2,3-Dihydro-3,3-dimethyl-1H-indol (9) und 2-[(1-Hydroxy-2-methyl)-2-propyl]-anilin (10).相似文献