18456-44-5Relevant academic research and scientific papers
Diastereoselective synthesis of 2,6-diaryltetrahydrothiopyran-4-ones by phase-transfer catalysis
Gendron, Thibault,Kessedjian, Hripsimée,Davioud-Charvet, Elisabeth,Lanfranchi, Don Antoine
, p. 1790 - 1796 (2015)
Two efficient phase-transfer-catalyzed protocols for the diastereoselective synthesis of cis and trans isomers of 2,6-diaryltetrahydrothiopyran-4-ones (2,6-DATHTPs) have been developed. In a study of the scope of the reactions, differently substituted 2,6
Spectral characterization and crystal structure of some 2,6-diarylthian-4-one hydrazone derivatives
Sankar,Umamatheswari,Pandiarajan
, p. 554 - 563 (2015/01/08)
A series of cis and trans 2,6-diarylthian-4-one hydrazone derivatives (11-16) have been synthesized and characterized by 1H, 13C and two dimensional NMR spectroscopy. For the 2r,6t-diphenylthian-4-one N-isonicotinoylhydrazone (14) X-ray diffraction have also been recorded. The coupling constants suggested that the cis-hydrazones (11-13), which have the phenyl groups in cis orientation, largely exist in chair conformations with equatorial orientation of the phenyl groups 11C. Analysis of the vicinal coupling constants of trans-hydrazones (14-16) suggests that boat forms 14B must make significant contributions to it and the relative population is 58%. Moreover, in solution chair conformations 14C and 14C′, may contribute to 14. The NOESY and X-ray diffraction of 14 gives definite evidence for the contribution of 14C.
Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
Parthiban, Paramasivam,Aridoss, Gopalakrishnan,Rathika, Paramasivam,Ramkumar, Venkatachalam,Kabilan, Senthamaraikannan
supporting information; experimental part, p. 2981 - 2985 (2010/03/03)
Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs.
Tetrahydrothiapyran-4,ones - Source for annelated 1,2,3- selena/thiadiazoles and their reactivity
Bhaskar Reddy,Somasekhar Reddy,Subba Reddy
, p. 1342 - 1348 (2007/10/03)
1.2.3-Selenadiazole 4 and 1,2,3-thiadiazole 5 rings have been fused to 2.6-diaryl-(3-alkyl) tetrahydrothiapyran-4-ones 2 utilising α-ketomethylene group. The reactivity of the latter has also been studied viz., Beckmann rearrangement, Shapiro reaction. Strecker synthesis of α aminoacids etc.
Syntheses of 4H-thiopyran-4-one 1,1-dioxides as precursors to sulfone-containing analogues of tetracyanoquinodimethane
Rule,Detty,Kaeding,Sinicropi
, p. 1665 - 1673 (2007/10/02)
Synthetic routes to the unsubstituted 4H-thiopynan-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation of 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.
An efficient synthesis of cis-2,6-diaryl-1-methyl-4-piperidones
Vijayabaskar, Veerappan,Perumal, Subbu,Devanathan, Vangeepuram Canchi
, p. 649 - 651 (2007/10/03)
cis-2,6-Diaryl-1-methyl-4-piperidones have been synthesised in excellent/yields (85-93percent) by the reaction of triarylideneacetylacetones (1) with methylamine in dimethyl formamide at room temperature.This reaction presumably proceeds vis Michael addit
Phase Transfer-Catalyzed Reactions between Polysulfide Anions and α,β-Unsaturated Carbonyl Compounds
Krein, Eitan B.,Aizenshtat, Zeev
, p. 6103 - 6108 (2007/10/02)
Ammonium polysulfide reacts with α,β-unsaturated ketones and aldehydes under PTC (phase transfer catalysis) conditions in a rather different manner than it does in homogeneous systems. 1,3-Diphenyl-2-propen-1-one (chalcone, 1) and 4-phenyl-3-buten-2-one (
Steric Effects in the Oxidation of Oxan-4-ols and Thian-4-ols by Vanadium(V)
Arjunan, Periaswamy Gounder,Lakshmanan, Joghee Gowder,Chandrasekara, Nallappan,Ramalingam, Kondareddiar,Selvaraj, Kuppusamy
, p. 1183 - 1186 (2007/10/02)
The rates of oxidation of 20 heterocyclic alcohols by vanadium(V) have been measured at 60 deg C in aqueous acetic acid medium in the presence of sulfuric and perchloric acid.The data indicate an overall second-order reaction at constant acid concentration, first-order each in alcohol and oxidant.The conformational effects on the rates of oxidation of various heterocyclic alcohols are discussed.An interesting observation in the present study is that t-2,t-6-diphenyl-c-3,c-5-dimethyloxolan-r-4-ol, an axial alcohol, reacts slower than corresponding equatorial epimer, c-2,c-6-diphenyl-t-3,t-5-dimethyl-oxan-r-4-ol, which is contrary to general expectations.
cis-2,6-Diphenyl-4-piperidones and Their Derivatives : A PMR Spectral Study
Sivasubramanian, S.,Sundharavadivelu, M.,Arumugam, N.
, p. 878 - 879 (2007/10/02)
In addition to the expected features, the PMR spectra of cis-2e,6e-diphenyl-4-piperidones and their N-methyl derivatives show unusually broad aromatic proton signals with concurrent multiplicity.This characteristic broadening and multiplicity of the aroma
Photoisomerisation of 2,6-Diphenyltetrahydrothiapyran-4-one
Pillay, M. Krishna,Chellaraj, David A. J.
, p. 327 - 328 (2007/10/02)
Photolysis of methanolic solutions of cis-(1) and trans-(2)-2,6-diphenyltetrahydrothiapyran-4-ones results in the formation of an equilibrium mixture of 1 and 2, in which 1 predominates.A possible mechanism involving α-cleavage followed by ring closure has been presented.
