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1.
Several substituted terphenyl derivatives were prepared following two synthetic routes with five steps. Condensation of 4‐amino‐3‐bromo‐benzotrifluoride with 4‐(methylthio) phenyl boronic acid in the presence of sodium carbonate and palladium triphenylphosphine in toluene gave 4‐amino‐3‐(4‐methylthiophenyl)‐benzotrifluoride. Treatment of this compound with osmium tetroxide in the presence of 4‐methyl morpholine‐N‐oxide yielded the corresponding sulfone, which was converted into the iodo derivative using sodium nitrite. The iodo derivative thus obtained was treated first with propylmagnesium chloride and triethylborane and subsequently with hydroxylamine‐O‐sulfonic acid to furnish the target compounds. 相似文献
2.
The optical transient and kinetics characterizations of the transients formed in the reaction of OH with benzotrifluoride (BTF) were performed by a laser flash photolysis technique. The results indicated that the formation of π‐type adduct of C6H5(OH)CF3 was the major reaction channel, and the δ‐type adduct of C6H5CF3OH formation was an additional minor process in the oxidation reaction of BTF attacked by OH radicals yielded from the photolysis of H2O2. Addition of OH to the CF3 group led to the fluoride ion elimination to yield α,α‐difluorophenylcarbinol (C6H5CF2OH). Trifluoromethylphenol (HOC6H4CF3) of meta‐, para‐ and ortho‐substituted isomers resulted from the addition of OH to the BTF aromatic ring. 相似文献
3.
G. K. Pierens T. K. Venkatachalam D. Reutens 《Magnetic resonance in chemistry : MRC》2014,52(8):453-459
Ortho‐substituted and para‐substituted aminophenyl benzothiazoles were synthesised and characterised using NMR spectroscopy. A comparison of the proton chemical shift values reveals significant differences in the observed chemical shift values for the NH protons indicating the presence of a hydrogen bond in all ortho‐substituted compounds as compared to the para compounds. The presence of intramolecular hydrogen bond in the ortho amino substituted aminophenyl benzothiazole forces the molecule to be planar which may be an additional advantage in developing these compounds as Alzheimer's imaging agent because the binding to amyloid fibrils prefers planar compounds. The splitting pattern of the methylene proton next to the amino group also showed significant coupling to the amino proton consistent with the notion of the existence of slow exchange and hydrogen bond in the ortho‐substituted compounds. This is further verified by density functional theory calculations which yielded a near planar low energy conformer for all the o‐aminophenyl benzothiazoles and displayed a hydrogen bond from the amine proton to the nitrogen of the thiazole ring. A detailed analysis of the 1H, 13C and 15N NMR chemical shifts and density functional theory calculated structures of the compounds are described. Copyright © 2014 John Wiley & Sons, Ltd. 相似文献
4.
Various new substituted and fused pyridotriazepine analogues have been synthesized via different synthetic pathways. Among which are different heterocyclic compounds consisting of the pyridotriazepine backbone fused to different heterocyclic systems comprising either substituted pyrimidine nucleus such as compounds 3 – 9 or substituted 4‐aminopyridine nucleus such as compounds 10 – 16 . Besides, the tetrahydroquinoline derivative 17 , [1,2,4]triazolopyrimidine derivative 18 , thienodiazocine derivative 19 , dihydrobenzofuropyridine derivative 20 , and the substituted pyrrole derivative 21 were synthesized. In addition, different substituted pyridotriazepine derivatives as indicated in compounds 22 – 25 were designed and synthesized. Twenty‐five of the newly synthesized compounds were subjected to in vitro anticancer screening against mammalian colon carcinoma HCT‐116 cell line using Cisplatin as a reference drug. The anticancer activity screening results revealed that among the tested compounds, the tetrahydropyrido[1,2‐b]pyrimido[4,5‐e][1,2,4]triazepine derivative 4 substituted at C2 and C4 positions with S‐methyl and amino moieties, respectively, and the 2,4‐dithioxo analogue 9 and the 2‐thioxodipyrido[1,2‐b:2′,3′‐e][1,2,4]triazepine derivative 11 substituted at C3 and C4 with a cyano and amino moieties, respectively, exhibited moderate to strong anticancer activity against mammalian colon carcinoma HCT‐116 cell line. 相似文献
5.
Wael A. El‐Sayed Omar M. Ali Merfat S. Faheem Ibrahim F. Zied Adel A.‐H. Abdel‐Rahman 《Journal of heterocyclic chemistry》2012,49(3):607-612
New [1,2,4‐oxadiazolyl]methyl‐3H‐[1,2,3]triazolo[4,5‐d]pyrimidin derivatives were synthesized starting from N′‐Hydroxy‐1‐naphthimidamide. The N‐substituted acyclic nucleoside analogs as well as the substituted glycosides were also prepared by reaction with the corresponding reagents. The antimicrobial results indicated that most of the tested compounds exhibited moderate to high antimicrobial activity whereas few compounds were found to exhibit little or no activity against the tested microorganisms. 相似文献
6.
Hiroyuki Tsuchida 《Tetrahedron》2010,66(19):3447-6538
Ferric chloride (FeCl3) promoted electron transfer oxidation of bicyclic cyclopropyl silyl ethers was performed in biphasic solution system of 1-butyl-3-methylimidazolium hexafluorophosphate (BmimPF6) and benzotrifluoride (BTF). The resulting chloro-substituted ring-expanded cycloalkanones were treated with an appropriate base to produce substituted cyclic enones. These two-step reactions were successfully devised to proceed in a simpler manner in which the ordinary work-up operations for the former oxidation step, such as water-quench, extraction, and evaporation, were omitted; imidazole was found to be the most suitable base for the latter elimination step. 相似文献
7.
Omar M. Ali Wael A. El‐Sayed Heba A. El‐Sayed Adel A.‐H. Abdel‐Rahman 《Journal of heterocyclic chemistry》2012,49(5):1026-1032
New thiazole derivatives were synthesized. The N‐substituted acyclic nucleoside analogs and the substituted glucosides were also prepared. The synthesized compounds were tested for their antimicrobial activity against Candida albicans, Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The obtained results indicated that most of the tested compounds exhibited low to high moderate activities whereas few compounds were found to exhibit little or no activity against the tested microorganisms. 相似文献
8.
Design and Synthesis of 3‐Substituted‐thiazolyl‐2‐iminothiazolidin‐4‐ones as a New Class of Anticonvulsants
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V. Alagarsamy M. Senthilraja V. Raja Solomon 《Journal of heterocyclic chemistry》2016,53(5):1635-1639
A new series of 3‐substituted‐thiazolyl‐2‐iminothiazolidin‐4‐ones were synthesized by nucleophilic substitution of p‐substituted‐thiazol‐2‐yl‐chloroacetamides with potassium thiocyanide by cyclization. The starting material p‐substituted‐thiazol‐2‐yl‐chloroacetamides were synthesized from p‐substituted‐thiazol‐2‐yl‐amines with chloroacetyl chloride, which in turn was prepared from one pot reaction of substituted aryl acetophenone and amino group of thiourea. The title compounds were investigated for their anticonvulsant activity. Among the tested compounds, compound 3‐(4‐(4‐fluorophenyl)thiazol‐2‐yl)‐2‐iminothiazolidin‐4‐one ( 16 ) emerged as the most active compound of the series, and it is moderately more potent than the reference standard diazepam. 相似文献
9.
Zhong‐Xia Wang Li‐Zhuang Chen Bei Li Guang‐Fan Han 《Journal of heterocyclic chemistry》2015,52(6):1663-1668
The Gewald reactions of 5‐substituted‐1,3‐cyclohexanedione, malononitrile, and powdered sulfur were carried out to give the corresponding products 2‐amino‐5‐substituted‐7‐oxo‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile derivatives 1 . The intermediate enamines 2 were prepared by reaction of compounds 1 and 5‐substituted‐1,3‐cyclohexanedione with hydrochloric acid as catalyst. The title compounds 11‐amino‐2,8‐substituted‐2,3,8,9‐tetrahydrobenzo[4,5]thieno[2,3‐b]quinolinone 3 were synthesized by cyclization of compounds 2 in the presence of K2CO3 and Cu2Cl2. The structures of all compounds were characterized by elemental analysis, IR, MS, and 1H‐NMR spectra. 相似文献
10.
Nirupam Das Biswajit Dash Meenakshi Dhanawat Sushant Kumar Shrivastava 《Chemical Papers》2012,66(1):67-74
Ten derivatives of N1 substituted/unsubstituted 5-(4-chlorophenyl)-3-(2-thienyl) pyrazoline were synthesised from chalcone-like
intermediate and substituted phenyl hydrazines, hydrazine hydrate, and semi/thiosemicarbazide. The chemical structure of compounds
was confirmed by means of IR, 1H NMR, mass spectroscopy, and elemental analysis. The antidepressant and anticonvulsant activities were investigated by Porsolt’s
behavioural despair test (forced swimming) and maximum electroshock seizure test, respectively. Rota-Rod test was performed
to assess any probable changes in motor coordination induced by the test compounds. Four compounds (IId, IIg, IIi, and IIj) exhibited good activity profile against depression and docking studies confirmed their consensual interaction with monoamine
oxidase A. In addition, compounds IIc and IIe showed protection against MES-induced seizures. 相似文献
11.
Frdric Leroux TilmanU. Hutschenreuter Cline Charrire Rosario Scopelliti RolfW. Hartmann 《Helvetica chimica acta》2003,86(7):2671-2686
3,3′,5,5′‐ And 2,2′,6,6′‐tetrafluoro‐substituted 1‐[(1,1′‐biphenyl]‐4‐yl)methyl]‐1H‐imidazoles were synthesized as inhibitors of 17α‐hydroxylase‐C17,20‐lyase (P450 17, CYP 17). P450 17 is the key enzyme of androgen biosynthesis. Its inhibition is a novel therapeutic approach for treatment of prostate cancer. To increase the so‐far insufficient in vivo lifetime of such compounds, the metabolically sensitive positions were blocked by F‐substitution. The meta‐ and ortho‐F‐substituted compounds were prepared by selective metallation or halogen/metal permutation reactions performed on symmetrically substituted 1,1′‐biphenyls. Compared with the halogen‐free compounds, the ortho‐F‐substituted derivatives did not match the activity, whereas the meta‐F‐substituted isomers equaled or surpassed the latter. 相似文献
12.
Cemil İbis Sibel Sahinler Ayla Neslihan Beyazit Hakan Bahar 《Phosphorus, sulfur, and silicon and the related elements》2013,188(11):1643-1651
Abstract Thiosubstituted butadiene and butenyne compounds were synthesized from the reactions of 1,1,3,3,4,4-hexachloro-1-butene or 1,1,2,4,4-pentachlorobuta-1,3-diene with different thiols in EtOH/H2O solution of NaOH. Tris(thio)substituted butadiene compound was treated with potassium tert-butoxide to obtain tris(thio)substituted butatrienyl halide compound. The novel sulfoxide compounds were synthesized from the reactions of polyhalobutadiene compounds with aliphatic thiols in CHCl3 with m-CPBA at 0°C. The structures of the novel compounds were characterized by micro analysis, FT-IR, 1H-NMR, 13C-NMR, and MS. 相似文献
13.
Novel substituted benzoquinone compounds were synthesized from the reactions of p-chloranil and p-fluoranil with some thiols, amines, and diols in different reaction media. Interesting cyclic compounds like crown ether structures were obtained. The structures of all compounds were characterized by spectroscopic methods and microanalysis. 相似文献
14.
《Journal of heterocyclic chemistry》2018,55(3):685-691
A new series of compounds containing thiazole nucleus as Rhodanine analogues have been synthesized. The new compounds were prepared from the reactions of the thiosemicarbazones ( 3a,b ) with a series of α‐halo carbonyl compounds to give the corresponding Rhodanine analogues. The thiosemicarbazones derivatives ( 3a,b ) were reacted also with hydrazonoyl chlorides to afford the corresponding tri‐substituted and tetra‐substituted thiazoles. The structures of the newly synthesized compounds were confirmed by elemental analysis and spectral data. The biological activities of the new synthesized Rhodanine analogues' were evaluated for their antimicrobial activities. The results showed that some of these compounds showed excellent activity against two fungal strains, including Aspergillus niger and Aspergillus flavus, in addition to three yeast strains, including Saccharomyces cervesi, Candida albicans NRRL Y‐477, and Candida Pathological specimen compared with the ketoconazol, as the reference drug. 相似文献
15.
Roberto Lava Emilia Aimo Luciana Menegus Giulio Pojana Antonio Marcomini 《Analytica chimica acta》2013
Two simple analytical methods for the simultaneous determination and quantification of benzotrifluoride and eight chlorinated, amino and nitro benzotrifluoride derivatives in groundwater are proposed. Benzotrifluoride, 4-chlorobenzotrifluoride, 2,4-dichlorobenzotrifluoride and 3,4-dichlorobenzotrifluoride, were extracted by Purge-and-Trap on the basis of their volatile properties, while 3-aminobenzotrifluoride, 4-nitrobenzotrifluoride, 3-amino-4-chlorobenzotrifluoride, 3-nitro-4-chlorobenzotrifluoride and 4-chloro-3,5-dinitrobenzotrifluoride extractions were done with an automated SPE system. The analytical separations and detections were performed with two different GC systems, both equipped with single quadrupole mass spectrometer as detector. The LOD ranges for the two methods were 0.002–0.005 μg L−1 and 0.01–0.07 μg L−1, respectively. Both extraction methods were developed using spiked Milli-Q water and were then demonstrated with groundwater samples collected during autumn 2008. The areas of groundwater collection were polluted due to an episode of improper industrial soil disposal and consequent leakage of aliphatic and aromatic, fluorinated chemicals into the groundwater. This work eventually revealed the presence of several benzotrifluoride compounds most of them, like dichloro- and amino-derivatives, never been reported as environmental contaminants. 相似文献
16.
A Regioselective Synthesis of Benzopinacolones through Aerobic Dehydrogenative α‐Arylation of the Tertiary sp3 CH Bond of 1,1‐Diphenylketones with Aromatic and Heteroaromatic Compounds
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Nagnath Yadav More Dr. Masilamani Jeganmohan 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(3):1337-1342
A regioselective synthesis of symmetrical and unsymmetrical benzopinacolones through aerobic dehydrogenative α‐arylation at the tertiary sp3 C?H bond of substituted 1,1‐diphenylketones with aromatic and heteroaromatic compounds, in the presence of K2S2O8 in CF3COOH at room temperature, is described. The reaction is proposed to go via a carbocation intermediate, which could be generated directly from cleavage of the sp3 C?H bond of 1,1‐diphenylketone. Subsequent α‐arylation was achieved at the methene sp3 carbon atom of the substituted ketone. A variety of substituted aromatic and heteroaromatic compounds were compatible with this reaction. In addition, benzopinacolones were converted into sterically hindered, tetrasubstituted alkenes and polycyclic aromatic compounds. 相似文献
17.
18.
This paper describes reactions of 3-bromo- 1a-d , 2-phenylthio- 5a-d and 2-phenylthio-3-bromofuropyridines 6a-d with n-butyl-, t-butyl- and methyllithium and lithioacetonitrile. Lithiation of compounds 1a-d with n-butyl- or methyllithium gave the parent furopyridines 2a-d and o-ethynylpyridinols 3a-d. Reaction of compounds 5a-d with methyllithium afforded o-(phenylthioethynyl)pyridinols 7a-d , which were also yielded by reaction of compounds 6a-d with t-butyl- or methyllithium. The phenylthio group in compounds 7a-d were substituted with t-butyl group by the reaction with excess t-butyllithium. In contrast, 2-phenylthio group in compounds 5a-d and 6a-d was substituted with cyanomethyl group by reaction with lithioacetonitrile to give compounds 11a-d and 10b, c respectively. 相似文献
19.
Jean-Louis Kraus Philippe Dugenet Jean-Jacques Yaouanc 《Journal of heterocyclic chemistry》1982,19(4):971-973
The synthesis of new 3,5 dioxo-1,2,4 oxadiazolidines whixh are N-2 substituted bioisosters of biologically active carboxylic compounds was studies. Nitro compounds were used as starting materials, and triton B as the cyclizing base. The expected N-2 allyl and aryl substituted derivatives were obtained in satisfactory yields. 相似文献