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1.
A. Y. Hassan 《Phosphorus, sulfur, and silicon and the related elements》2013,188(11):2759-2776
The reaction of thiocarbohydrazide with carboxylic acids at the melting temperature allows an improved preparation of 5-substituted-4-amino-3-mercapto 1,2,4-triazoles 1 a ? g . Compound 1 a reacted with 2-bromopropionic acid to give acid derivative 2 . The latter was reacted with a mixture of acetic anhydride and triethylamine to afford the mesoionic compound 3 . Heating of compound 3 in ethanol gave the ester derivative 4 , which on alkaline hydrolysis in methanol gave ketone derivative 5 . Substituted 1,2,4-triazolo [3,4-b]-6H-1,3,4-thiadiazine 6 h,i and 7 were synthesized by reaction of 1 a with acetylacetone, ethyl acetoacetate and chloroacetamide. Heterocyclic systems 8 and 9 were prepared through the reaction of 1 a with 2,3-dichloro-1,4-naphthoquinone and 2,3-dichloroquinoxaline. In addition, thenoyl isothiocyanate, thenoyl chloride, 2-thiophenecarbaldehyde, and p-chlorophenyl isocyanate reacted with compound 1 a to afford 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole ring system 10 , 11 , and urea derivative 12 . 1,2,4-Triazolo[3,4-b]-5H-pyrazole derivatives 14 j,k were prepared through the reaction of compound 1 a with 3-chloro-2,4-pentandione and ethyl-2-chloroacetoacetate. Compound 14 j was treated with hydrazine to afford products 15 , 16 , and 17 depending on the type of hydrazine derivative and reaction conditions. Compound 19 was synthesized by refluxing of compound 14 j with hydroxylamine hydrochloride to afford the corresponding oxime derivative 18 followed by treatment with thenoyl chloride. 相似文献
2.
Cemil İbiş Zeliha Gökmen 《Phosphorus, sulfur, and silicon and the related elements》2013,188(4):939-945
Mono(thio)substituted dienes 1 gave 3a–g , 5 , and 7 with piperazine derivatives in dichloromethane. Hexachlorobutadiene 14 in a water-ethanol mixture in the presence of sodium hydroxide reacted with thiol 15 to give the mono(thio)substituted thioether 16 and di(thio)substituted thioether 17 . 18 was obtained from the reaction of 16 with m-CPBA in chloroform. 9 was obtained from the reaction of l,2,3,4,4-pentachloro-(1-2-hydroxyethylthio)-1,3- butadiene 8 with 47% HI, and 11 was synthesized from the reaction of 8 with concentrated H2SO4 and KBr. Compounds 9 and 11 gave in the reaction with m-CPBA in chloroform 10 , 12 , and 13 , respectively. 相似文献
3.
Md. Manzoor Hussain Mohammed Shafi G. Narayana Swamy S. G. Peeran 《Phosphorus, sulfur, and silicon and the related elements》2013,188(4):763-770
The addition of benzenethiol to p-chlorophenylphenylacetylene results in the formation of a mixture of two pairs of diastereomeric (E)- and (Z)-1-p-chlorophenyl-2-phenyl-1-phenylthioethylenes (1 and 2) and (E)- and (Z)-1-p-chlorophenyl-2-phenyl-2-phenylthioethylenes (3 and 4). The configurations of these compounds have been established by 1 H NMR studies, by their preparation from benzyl p-chlorophenyl ketone and p-chloro-benzylphenyl ketone, and by the oxidation of the thioethylenes 1, 2, 3, and 4 to the corresponding sulphonylethylenes 5, 6, 7, and 8, respectively. 相似文献
4.
Tchicama Mella Mamane Zied Hassen Béchir Hajjem 《Phosphorus, sulfur, and silicon and the related elements》2013,188(11):2854-2864
The cyanomethylphosphonates 1 and the ethyl phosphoacetates 2 were reacted with some fluorophenylisothiocyanates to give the 2-thioxoethylphosphonates 3 in tautomeric equilibrium with the corresponding 2-mercaptovinylphosphonates 3 ′ and the 2-phosphoryl-3-thioxopropanoates 4 , respectively. Reaction of the cyanomethylphosphonates 1 with fluorophenylisothiocyanates in presence of methyliodide furnished the 2- thiometylvinylphosphonates 5 . The 2-mercaptovinylphosphonates 3 ′ reacted with ethyl chloroacetate in refluxing ethanol in the presence of triethylamine to give S-substitued derivatives 6 . 相似文献
5.
Henryk Foks Danuta Pancechowska-Ksepko Mieczysław Janowiec Zofia Zwolska Ewa Augustynowicz-Kopeé 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2291-2297
1,1-bis-methylthio-2-nitro-ethene was used as a substrate to the syntheses of new heterocyclic compounds. In the reactions, with 1-phenylpiperazine—the corresponding diaminonitroethane 1 , 1,3-diaminonitropropane, and 1,3-diaminonitropropanol—the nitromethylenotetrahydropyrimidine derivatives 2 and 3 were prepared, whereas, with o-phenylenediamine—2-nitromethyleno-benzimidazole 4 were obtained. In the condensation reactions of compounds 2 , 3 , and 4 with benzoyl isothiocyanate, the products 5 , 6 , and 7 were obtained, and afterwards two of them, 5 and 6 , were transformed into the isothiazolines 8 and 9 . 1,1-bis-(4-phenylpiperazino)-2-nitroethane ( 1 ) was exposed to the action of phenyl isothiocyanate and the derivative obtained ( 10 ) was transformed, in the reaction with phenacylbromide, in to benzoylonitrothiophene 11 . The diazo compounds 12 , 13 , and 14 were obtained in the reactions of nitromethylenotetrahydropyrimidines 2 and 3 and of 2-nitromethylenobenzimidazole 4 with benzenediazonium chloride. The derivatives obtained were tested in vitro for their tuberculostatic activity. The compounds 7 (MIC 8–32 μg/mL) and 14 (MIC 16–63 μg/mL) appeared to be the most active compounds. 相似文献
6.
W. Adam J. Halász Z. Jámbor A. Lévai C. Nemes T. Patonay G. Tóth 《Monatshefte für Chemie / Chemical Monthly》1996,127(6-7):683-690
Summary Oxidation of the (E) and (Z) isomers of 2-arylidene-1-indanones (1) and 2-arylidene-1-benzosuberones (4) by alkaline hydrogen peroxide (methodi) afforded the spiroepoxidestrans-2a–g andtrans-5a–g from both isomers as sole products in high yields. On the other hand, dimethyldioxirane epoxidation(methodii) of the (E) isomers1a–g and4a–g gave the correspondingtrans spiroepoxides in good yields, whereas the (Z) isomers1a,c,e and4a,c,e led to thecis spiroepoxides in moderate yields. Dimethyldioxirane oxidation (methodii) of (Z)-1c and (Z)-4c,e gave diones3c and6c,e as by-products as well. Epoxidation of (Z)-1a,c,e and (Z)-4a,c,e bym-chloroperoxybenzoic acid (methodiii) resulted inca. 6:1 mixtures ofcis-2a,c,e andtrans-2a,c,e orcis-5a,c,e andtrans-5a,c,e spiroepoxides.Dedicated to Prof.W. Fleischhacker on the occasion of his 65th birthday 相似文献
7.
Abdullah G. M. Al-Sehemi 《Phosphorus, sulfur, and silicon and the related elements》2013,188(8):1991-2003
The starting material 1,2,4-triazole derivative ( 3 ) was used to synthesize some novel condensed triazoles. Thus, treatment of compound ( 3 ) with phenyl isocyanate in refluxing pyridine furnished the novel [1,2,4]triazolo[4,3-b][1,2,4]triazole derivative ( 5 ). Also, cyclization of compound ( 3 ) with phenyl isothiocyanate afforded the [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivative ( 7 ). Hydrazone derivative ( 9d ) was allowed to react with some halogenated reagents such as chloroacetone, ethyl chloroacetate, and chloroacetonitrile to furnish thiazole derivatives ( 12 ), ( 13 ), and ( 15 ), respectively. In a similar manner, bishydrazone ( 17 ) was used to prepare the novel bisthiazoles ( 18 ) and ( 19 ). Some of the synthesized compounds were evaluated for their antibacterial activity. 相似文献
8.
The in vitro microsomal metabolism of JWH-015, a ligand that exhibits a high binding affinity at the peripheral cannabinoid
receptor CB2, has been studied. A total of 22 metabolites were identified and structurally characterized. The metabolites are products
of: 1) monohydroxylation on the naphthalene ring (m/z 344, M20 and M21), indole ring (m/z 344, M17 and M18), or the N-alkyl group (m/z 344, M14); 2) arene oxidation leading to dihydrodiols (m/z 362, M12 and M15); 3) dihydroxylation on the naphthalene ring (m/z 360, M7) or indole ring (m/z 360, M13), resulting from a combination of monohydroxylations on both the naphthalene and indole rings (m/z 360, M16), or a combination of monohydroxylations on the naphthalene ring and on the N-propyl group (m/z 360, M9); 4) trihydroxylation (m/z 378, M1, M3, M4, M6, and M10); 5) N-dealkylation (m/z 286, M19); 6) N-dealkylation and monohydroxylation on the naphthalene ring (m/z 302, M11); 7) N-dealkylation and dihydrodiol formation from arene oxidation (m/z 320, M2 and M5); 8) dehydrogenation after monohydroxylation on the N-alkyl group (m/z 326, M22); 9) dehydrogenation and monohydroxylation on the indole ring (m/z 342, M8). 相似文献
9.
A. M. Kamal El-Dean A. M. Elkhawaga Sh. M. Radwan M. M. Ahmed 《Phosphorus, sulfur, and silicon and the related elements》2013,188(8):2034-2048
Mercaptomethylpyrazolopyrimidine (2) was synthesized and reacted with ethyl chloroacetate to afford ethyl pyrazolpyrimidinylmethylmercapto acetate ( 3) , which in turn was converted into the corresponding carbohydrazide 4 . Carbohydrazide 4 reacts with a variety of reagents to give different pyrazolopyrimidines ( 5–12 ). Chloromethyl-pyrazolopyrimidine (1) reacts with chloropyridine to give compound 13 , which was subjected in a series of reactions to give new compounds 14–20 . 相似文献
10.
Application of Vilsmeier–Haack reaction on 4,6-diacetylresorcinol (1) led to the formation of 4,6-dioxo-4H,6H-pyrano[3,2-g]chromene-3,7-dicarboxaldehyde (2) in good yield. The dicarboxaldehyde 2 was condensed with some carbon and nitrogen nucleophiles. Some aliphatic and aromatic Schiff bases of 4,6-diacetylresorcinol (1) were subjected to Vilsmeier–Haack formylation reaction to afford 4,6-bis(alkyl/arylimino)-4H,6H-pyrano[3,2-g]chromene-3,7-dicarbaldehydes 10, 14, and 15. Also, treatment of some bis-hydrazones of 4,6-diacetylresorcinol 16–19 with Vilsmeier–Haack reagent afforded the corresponding 4,6-bis(4-formylpyrazol-3-yl)resorcinols 20 and 21, which underwent oxidation with iodine to yield the pyrano[3,2-g]chromeno[4,3-c:7,6-c]dipyrazole-4,8-diones 22 and 23, respectively. Most of the synthesized compounds revealed weak antimicrobial activities. It was noticed that the dicarboxaldehydes 2, 10, 14, and 15 exhibited moderate antibacterial activity against Gram-positive bacteria, yeast, and fungus. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] 相似文献
11.
Katarzyna Spalińska Henryk Foks Anna Kedzia Marta Wierzbowska Ewa Kwapisz Alina Gebska 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3):609-625
The synthesized series of new thiosemicarbazide derivatives ( 1 , 6–10 ) in reactions with carbon disulphide produced, according to the reaction conditions, the dithioacids ( 4 , 30 ) or the 5-substituted 1,3,4-thiadiazolo-2-thiol derivatives ( 2 , 27 ). The dithioacids were cyclized, in the reaction with hydrazine, into the 4-ami-no-1,2,4-triazolo-2-thiol derivatives ( 5 , 31 ). One of these compounds ( 31 ) was transformed into the 1,2,4-triazolo-1,3,4-thiadiazine derivative ( 33 ). The compo-unds 6–9 were also exposed to the condensation with aldehydes. 4-phenylpipera-zinocarbothiohydrazide ( 6 ) was exposed to the action of isothiocyanates, which gave the compounds 16–20 , and these cyclized to the 1,3,4-thiadiazoloamino derivatives ( 21–23 ). The susceptibility of aerobic and anaerobic bacteria to some of the new derivatives were tested. The anaerobes were the most susceptible at concentrations in ranges less than 6.2 to 100 μg/mL to derivative: 9 (64% were susceptible), 1 , 13 (for 60%), and 7 (for 56%). 相似文献
12.
Johannes Leitich Oskar E. Polansky Werner Riemer Ursula Ritter-Thomas 《Monatshefte für Chemie / Chemical Monthly》1982,113(4):485-494
Knoevenagel condensation of malononitrile withcis- andtrans-2,5-dimethylcyclohexanone (1
c and1
t, respectively) leads to2
c and2
t, respectively, and withtrans-1-decalone to4
t. The equilibria2
c2
t and4
c4
t have been determined as well as, by means of 270-MHz-1H-NMR, the conformations of these four compounds. The dicyanomethylene group is found to induce axial positions of neighbouring alkyl residues on the cyclohexane ring (or when this is impossible, as in the case of4
t, the twist form of the cyclohexane ring). This results in a strong predominance of thecis isomers in the equilibria2
c2
t and4
c4
t whereas thetrans isomers strongly predominate in the equilibria among the starting ketones. This situation allows the optional preparation of2
c or2
t, and of4
c or4
t, from the more stable starting ketone (or ketone mixture). The free conformational energy of the distorted twist form of4
t amounts to 17 kJ/mol.
Herrn Prof. Dr.E. Ziegler, Graz, zum 70. Geburtstag in aufrichtiger Verbundenheit gewidmet. 相似文献
13.
David R. Yarkony 《Theoretical chemistry accounts》1998,98(4):197-201
It is shown that the cross product t
I
J
(R
x
)≡g
I
J
(R
x
)×h
I
J
(R
x
), where g
τ
I
J
(R)=(c
I
(R
x
)−c
J
(c
I
(R
x
)+c
J
(R
x
)), h
τ
I
J
(R)=c
I
(R
x
)†
c
J
(R
x
), τ is an internal nuclear coordinate, the c
I
(R) satisfy [H(R)−E
I
(R)]c
I
(R)=0 and H(R) is the electronic Hamiltonian matrix, is a unique property of a conical intersection at R
x
. t
I
J
(R
x
)=0 when R
x
is located at the intersection of two (or more) seams of conical intersection. This criterion for an intersection of two
seams of conical intersection has important implications for algorithms that seek to locate such points. Here it␣is␣used to
analyze the trifurcation of a generic C2v
2S+1
A−2S+1
B seam of conical intersection, analogous to those recently found in AlH2 and CH2.
Received: 31 July 1997 / Accepted: 27 August 1997 相似文献
14.
ABSTRACT 3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (1) and 3,6-dideoxy-1,2-O-isopropylidene-α-D-glycero-hex-3-enofuranos-5-ulose (6) reacted with carbon disulfide and methyl iodide under basic conditions to give the α-oxoketene-S,S-acetals 2 and 7, respectively. Treatment of 2 and 7 with hydrazine hydrate yielded the pyrazole derivatives 3 and 8, respectively. 相似文献
15.
Michael Afolayan Radhakrishnan Srivedavyasasri Olayinka T. Asekun Oluwole B. Familoni 《Natural product research》2019,33(2):287-291
Phytochemical investigation of the methanolic extract of dried leaves of Bridelia ferruginea led to the isolation and identification of fourteen compounds (1–14): compound 1 [mixture of palmitic, stearic and oleic acids], stearyl monoester of 2-O-β-?-glucosylglycerol (2), 6β-hydroxy-(20R)-24-ethylcholest-4-en-3-one (3a), 6β-hydroxy-(20R)-24-ethylcholest-4,22-dien-3-one (3b), lutein (4), vomifoliol (5), corilagin (6), kaempferide-3-O-β-?-glucoside (7), myricetin (8), isomericitrin (9), isoquercetin (10), myricitrin (11), quercitrin (12), rutin (13), and β-sitosterol glucoside (14). The total extract exhibited moderate activity towards CB2 receptor and 90% inhibition against leishmanial pathogen Trypanosoma brucei. Compound 4 exhibited 73% displacement in CB2 receptor with IC50 56.47 μM, and 93% inhibition towards T. brucei with IC50 4.16 μM. Compound 11 showed 99% inhibition towards Escherichia coli with IC50 1.123 μM. 相似文献
16.
Hasan Kırmızıbekmez Yiğit İnan Rengin Reis Hande Sipahi Ahmet C. Gören Erdem Yeşilada 《Natural product research》2019,33(17):2541-2544
Phytochemical investigations on the EtOH extract of Clematis viticella led to the isolation of six flavonoid glycosides, isoorientin (1), isoorientin 3′-O-methyl ether (2), quercetin 7-O-α-L-rhamnopyranoside (3), quercetin 3,7-di-O-α-L-rhamnopyranoside (4), manghaslin (5) and chrysoeriol 7-O-β-D-glucopyranoside (6), one phenylethanol derivative, hydroxytyrosol (7), along with three phenolic acids, caffeic acid (8), (E)-p-coumaric acid (9) and p-hydroxybenzoic acid (10). The structures of the isolates were elucidated on the basis of NMR and HR-MS data. All compounds were isolated from C. viticella for the first time. Compounds 7 and 8 showed significant anti-inflammatory activity at 100 μM by reducing the release of NO in LPS-stimulated macrophages comparable to positive control indomethacin. Compounds 3 and 7 exhibited anti-inflammatory activity through lowering the levels of TNF-α while 1, 3 and 5 decreased the levels of neopterin better than the positive controls. 相似文献
17.
Stereoselective syntheses on a gram scale of (3Z,6E,8E)-, (3Z,6E,8Z)-and (3Z,6Z,8Z)-3,6,8-dodecatrien-1-ol, 8, 9 and 10, respectively, are described. A key step of the synthesis of 8 consisted of a copper-mediated coupling reaction between 4-(2-tetrahydropyranyloxy)-1-butynylmagnesium bromide (15) and the mesyl ester of (2E,4E)-2,4-octadien-1-ol (14). A similar copper-mediated reaction between 15 and the mesyl ester of (E)-2-octen-4-yn-1-ol (19) was used to construct the C-12 carbon skeleton of 9. On the other hand, the synthesis of 10 was based on a palladium-promoted reaction between (Z)-1-bromo-1-pentene (23) and the organozinc bromide derived from 3,6-heptadiyn-1-yl acetate (27). 相似文献
18.
Hanqing Zhao Huiqi Jia Hongxia Duan Jianjun Zhang Daoquan Wang Xiaomei Liang 《Journal of carbohydrate chemistry》2013,32(3):103-117
Synthesis of two isomeric tetrasaccharides, β-D-Glup-(1→2)-α-L-Rhap-(1→3)-α-L- Rhap-(1→2)-α-L-Rhap (I) and β-D-Glup-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap (II), the repeating units from the lipopolysaccharides of the nitrogen-fixing bacterium Azospirillum brasilense S17 and Azospirillum lipoferum SR65, was achieved via assembly of the building blocks 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate (2), p-methoxyphenyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside (3), 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (6), 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl trichloroacetimidate (8), and p-methoxy phenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside (14). Condensation of 3 with 6 or 8 provided the disaccharides 9 or 11, respectively. Deallyloxycarbonylation of 11 gave the disaccharide aceptor 12, while removal of the p-methoxyphenyl group in 9 followed by trichloroacetimidation of the anomeric hydroxyl group afforded the disaccharide donor 10. Meanwhile, disaccharide donor 16 and acceptor 18 were prepared from 6, 8, and 14 similarly. Finally, condensation of 10 with 12 or 16 with 18, followed by deprotection, gave the target tetrasaccharides I or II, respectively. 相似文献
19.
Cemil İbiş Nihal Onul 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):2787-2792
The substituted 1,2-dibromomethanethio nitrodiene 2 was obtained from the addition of bromine to S-substituted nitrodien 1 in carbon tetrachloride. N, S-substituted compounds 4a–h were synthesized from the reactions of compound 2 with several substituted piperazine derivatives 3a–h in dichloromethane. N, S-substituted compounds 6 and 8 were synthesized from the reaction of 2 with morpholine ( 5 ) and thiomorpholine ( 7 ) in dichloromethane, respectively. Dibutadienyl piperazines 10 , 12 , and 14 were synthesized from the reactions of 2 with homopiperazine ( 9 ), piperazine ( 11 ), and 2,5-dimethylpiperazine ( 13 ), respectively. 相似文献
20.
Alexander J. Blake Graeme Kirkpatrick Karen E. McGhie R. Michael Paton Kenneth J. Penman 《Journal of carbohydrate chemistry》2013,32(3):409-419
Abstract Benzonitrile oxide and ethoxycarbonylformonitrile oxide cycloadd regiospecifically and diastereoselectively to α-methyl 5,6-dideoxy-2,3-O-isopropylidene-d-lyxo-hex-5-enofuranoside 7 to afford isoxazolines 10 and 11. The π-facial selectivity (ca. 7:1) is comparable with that observed for xylo-alkene 1, and much greater than that for its ribo-isomer 4. The structure of isoxazoline 10a was determined by X-ray crystallography. 相似文献