- Synthesis and preliminary evaluation of the anti-cancer activity on A549 lung cancer cells of a series of unsaturated disulfides
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We synthesized a series of small symmetrical unsaturated disulfides by a multi-step reaction starting from organic alcohols, and we performed a preliminary test to evaluate the effect of these compounds on the viability of A549 lung cancer cells. The garlic-derived natural compound diallyl disulfide, known for its anticancer activity, was used as the lead compound in this study. We synthesized five DADS analogues having different carbon chain lengths and different positions of the double bonds. Two analogues exhibited a promising antitumor activity in vitro, and the allylic double bond did not seem to be the main driving force.
- Olivito, Fabrizio,Amodio, Nicola,Di Gioia, Maria Luisa,Nardi, Monica,Oliverio, Manuela,Juli, Giada,Tassone, Pierfrancesco,Procopio, Antonio
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Read Online
- Oxidation of some organic thiols with tetramethylammonium fluorochromate(VI)
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Tetramethylammonium fluorochromate oxidizes alcohols to the corresponding aldehydes and ketones without polymerization of double bonds, overoxidation, and other side reactions. This reagent is effective for oxidation of thiols to disulfides.
- Imanieh,Ghamami,Mohammadi,Jangjoo
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Read Online
- Trisulfides over disulfides: Highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles
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Temperature-and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-Transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.
- Bhattacherjee, Debojit,Sufian, Abu,Mahato, Sulendar K.,Begum, Samiyara,Banerjee, Kaustav,De, Sharmistha,Srivastava, Hemant Kumar,Bhabak, Krishna P.
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supporting information
p. 13534 - 13537
(2019/11/14)
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- Biocatalytic synthesis of diaryl disulphides and their bio-evaluation as potent inhibitors of drug-resistant Staphylococcus aureus
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Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time-kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi-drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2-bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration-dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti-staphylococcal therapy.
- Saima,Soni, Isha,Lavekar, Aditya G.,Shukla, Manjulika,Equbal, Danish,Sinha, Arun K.,Chopra, Sidharth
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p. 171 - 178
(2019/01/04)
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- A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water
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A one-pot and efficient synthesis of dialkyl dichalcogenides (S, Se) in aqueous media under catalyst-free conditions using benzylic, allylic and primary halides with elemental sulfur and selenium has been developed. Also, this procedure was extended to preparation of trisulfides and triselenides from secondary and tertiary halides in same condition. In all cases, products can be obtained in good to excellent yield in short reactions time.
- Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
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supporting information
p. 41 - 44
(2017/09/25)
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- Simple and green method for synthesis of symmetrical dialkyl disulfides and trisulfides from alkyl halides in water; PMOxT as a sulfur donor
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An environmentally new, mild and efficient method has been developed for the synthesis of dialkyl disulfides and dialkyl trisulfides in aqueous conditions by a reaction between alkyl halides (and tosylate) and potassium-5-methyl-1,3,4-oxadiazole-2-thiolate (PMOxT) as a sulfur transfer reagent. The advantages of this method are that it occurs under mild reaction conditions, it is base free, it uses water as the solvent and it occurs in high yields. A variety of dialkyl disulfides and dialkyl trisulfides can be obtained in good to excellent yields up to 98%.
- Soleiman-Beigi, Mohammad,Mohammadi, Fariba
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p. 134 - 141
(2017/03/07)
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- Europhtal (8020) efficiently catalyzes the aerobic oxidation of in situ generated thiols to symmetric disulfides (disulfanes)
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Efficient, odorless and scalable synthetic protocols have been introduced for the preparation of symmetric alkyl disulfides by treatment of the corresponding organic halides with thiourea and NaHCO3in the presence of commercially available Europhtal catalyst (8020) in both H2O and poly ethylene glycol (PEG-200) media at 80–90 °C. Structurally diverse primary, secondary, allylic and benzylic halides were examined successfully whereas, the result with tert-butyl bromide was not satisfactory. Also, another procedure has been introduced for achieving symmetric aryl disulfides in high yields by reacting aryl halides, thiourea and NaHCO3in PEG-200 at 115–120 °C using CuI along with Europhtal catalysts. The results showed that the aerobic oxidation of in situ generated thiols proceeded efficiently in the presence of Europhtal catalyst giving the symmetric disulfide without contamination by symmetric sulfide side-product.
- Abbasi, Mohammad,Sabet, Askar,Sabet, Askar
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- Conversion of organic halides to disulfanes using KCN and CS2
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A sulfur transfer reagent was produced in situ upon stirring a mixture of KCN and CS2 in DMF at r.t. for 15 min, which after heating with an alkyl halide or aryl halide and CuI gave the corresponding symmetric dialkyl or diaryl disulfide, respectively, in high to excellent yields.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Borazjani, Saeedeh Ghassab
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p. 4251 - 4254
(2017/10/11)
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- The synthesis of symmetrical disulfides by reacting organic halides with Na2S2O3·5H2O in DMSO
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A one-pot, and scalable method to prepare symmetric disulfides from their corresponding primary, secondary, allylic, and benzylic halides has been developed. In this method, a disulfide is synthesized by reacting an alkyl halide with Na2S2O3·5H2O at 60-70 °C in DMSO.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Saeedi, Narges
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supporting information
p. 89 - 92
(2016/01/12)
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- One-pot conversion of alkyl halides to organic disulfides (disulfanes) using thiourea and hexamethyldisilazane (HMDS) in DMSO
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A practical method to synthesize symmetric disulfides from alkyl halides has been developed. Using this procedure primary, secondary, benzylic and allylic disulfides were prepared by treating the corresponding alkyl halides with thiourea and HMDS in DMSO at 50 °C within 10-24 h in high yields.
- Abbasi, Mohammad,Jabbari, Arida
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- 4,4'-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea
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Heterocyclic azo compounds, prepared from corresponding amines in one step, are used as effective oxidants for the conversion of thiols into symmetrical disulfides in high yields. Among the studied azo compounds, 4,4'-azopyridine was found to be very efficient for the odorless conversion of alkyl halides into disulfides in the presence of thiourea. An attractive feature of this azo compound is that its obtained solid side product hydrazine is easily separated by filtration and can be recycled to its azo compound for further use.
- Khalili, Dariush,Iranpoor, Nasser,Firouzabadi, Habib
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p. 544 - 555
(2015/10/19)
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- One-pot synthesis of organic disulfides (disulfanes) from alkyl halides using sodium sulfide trihydrate and hexachloroethane or carbon tetrachloride in the poly(ethylene glycol) (PEG-200)
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Abstract Symmetric disulfides are produced by treating their corresponding organic halides including benzylic, allylic, primary and secondary halides with Na2S·3H2O and C2Cl6 or CCl4 in PEG-200 at room temperature in high yields.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Moosavi, Hekmat,Saeedi, Narges
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p. 1185 - 1190
(2015/03/31)
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- Bovine serum albumin triggered waste-free aerobic oxidative coupling of thiols into disulphides on water: An extended synthesis of bioactive dithiobis(phenylene)bis(benzylideneimine) via sequential oxidative coupling-condensation reactions in one pot from aminothiophenol and benzaldehyde
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Bovine serum albumin (BSA) has been explored for aerobic oxidative coupling of thiols (aromatic, heterocyclic as well as aliphatic) "on water" towards formation of disulphides (SS) without using any metal/non-metal complexes, bases and additives, which renders the process environmentally benign and economically attractive with good recyclability (up to four cycles). The developed green protocol was further extended for synthesis of diallyldisulphide (DADS), an important constituent of natural occurring allicin. Among various synthesized disulphides, bis(2-aminophenyl)disulphide, obtained by oxidative coupling of 2-aminothiophenol in BSA, was further utilized for condensation with benzaldehyde in the same pot thus enabling easy access to bioactive dithiobis(phenylene)bis(benzyldeneimine). This is the first example of BSA catalysed sequential (oxidation/condensation) reaction where one SS and two CN bonds are formed solely "on water."
- Saima,Lavekar, Aditya G.,Kumar, Rajesh,Sinha, Arun K.
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p. 113 - 123
(2015/04/14)
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- Graphene Oxide-Assisted One-Pot and Odorless Synthesis of Symmetrical Disulfides Using Primary and Secondary Alkyl Halides (Tosylates) and Thiourea as Sulfur Source Reagent
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Graphene oxide is described as a heterogeneous oxidant for the synthesis of symmetrical disulfides through the in situ generation of thiols from primary and secondary alkyl halides (tosylates) and thiourea in wet acetonitrile. A variety of alkyl halides and alkyl tosylates can be converted to corresponding disulfides in good to excellent yields. This strategy is free of foul-smelling thiols.
- Khalili, Dariush
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p. 1727 - 1734
(2015/12/12)
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- Direct synthesis of disulfides from alkyl halides using thiourea and CCl4 in glycerol
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Abstract Dialkyl disulfides were obtained on the basis of the reaction of alkyl halides and thiourea in the presence of CCl4 and Et3N. This procedure enables the odorless and one-pot synthesis of disulfides by employing cheap, easy-to-handle and readily available reagents and substrates in wet glycerol.
- Abbasi, Mohammad,Khalili, Dariush
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p. 1425 - 1430
(2015/06/22)
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- One-pot efficient synthesis of disulfides from alkyl halides and alkyl tosylates using thiourea and elemental sulfur without contamination by higher polysulfides
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An efficient and odorless synthesis of disulfides from alkyl halides using thiourea and elemental sulfur in the presence of sodium carbonate in wet polyethylene glycol (PEG 200) at 40 C without contamination by higher polysulfides has been developed. This procedure was then extended to preparation of disulfides from alkyl tosylates at 70 C.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Taghavi, Zeinab Khatoon
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p. 201 - 205
(2013/07/26)
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- Distinct catalytic effect of micellar solution of sodium dodecyl sulfate (sds) for one-pot conversion of alkyl halides to disulfides via an odourless process using thiourea and mno2
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A novel one-pot odourless synthesis of symmetrical disulfides from their corresponding halides in aqueous mediausing thiourea and MnO2 in the presence of NaHCO3 or Na2CO3 catalyzed by micellar solution of sodium dodecyl sulfate (SDS) is described. By this method, primary, allylic and benzylic halides were converted into their corresponding disulfides in high yields.
- Firouzabadi, Habib,Iranpoor, Nasser,Abbasi, Mohammad
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experimental part
p. 698 - 702
(2010/08/08)
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- A one-pot, efficient, and odorless synthesis of symmetrical disulfides using organic halides and thiourea in the presence of manganese dioxide and wet polyethylene glycol (PEG-200)
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Primary, secondary, tertiary, allylic, and benzylic halides are converted efficiently into symmetric disulfides in high yields using thiourea as the sulfur atom source. The reactions are odorless and are performed at 30-35 °C in wet PEG-200 using MnO2 as an oxidant.
- Firouzabadi, Habib,Iranpoor, Nasser,Abbasi, Mohammad
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experimental part
p. 508 - 509
(2010/10/02)
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- Easy and rapid method for disulfide syntheses using nanophase-manganese (VII) oxide coated clay
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Disulfide bond formation by the oxidation of several thiol compounds using nanophase manganese (VII) oxide coated clay (NM7O coated clay) in chlorinated, nonchlorinated (toluene), and polar solvents (water) is described. During the process, nitro and methoxy groups remain unaffected. The NM7O coated clay is easily prepared, stable, and inexpensive to manufacture. Furthermore, this and other studies prove that NM7O coated clay properties, i.e., mineralogy, chemical, and reactivity, are different from KMnO4. This rapid and facile synthesis coupled with the use of the recyclable NM7O coated clay catalyst will save energy due to low temperature and rapid reaction times, as well as minimal disposal problems, thus decreasing production costs.
- Gondi, Sudershan R.,Son, David Y.,Biehl, Edward R.,Vempati, Rajan K.
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scheme or table
p. 34 - 39
(2010/05/02)
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- The rapid and efficient synthesis of disulfides from alkyl and acyl halides
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Various symmetrical dialkyl and diacyl disulfides are prepared easily in high yields from the corresponding alkyl and acyl halides under mild and nonaqueous conditions using N,N'-dibutyl-N,N,N',N'-tetramethyl- ethylenediammonium tetrahydroborate (BTMETB) or N,N'-dibenzyl-N,N,N',N'- tetramethylethylenediammonium tetrahydroborate (BZTMETB) and elemental sulfur. The quaternary diammonium borohydrides were easily prepared by treatment of the corresponding quaternary diammonium chloride or bromide with alkaline solution of sodium borohydride at room temperature.
- Tajbakhsh, Mahmood,Lakouraj, Moslem M.,Mahalli, Majid S.
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experimental part
p. 1453 - 1456
(2009/12/04)
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- GARLIC PROCESSING
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A method of producing polysulfides comprising the step of adding elemental sulphur to an allicin-containing plant extract. In preferred embodiments, the plant extract is mechanically treated members of the genus Allium, especially garlic. In further preferred aspects of the invention, the plant extract and sulphur mixture is heated, and the pH is controlled to allow manipulation of the polysulfide chain length. The addition of organic bases, containing nitrogen lone pairs, allows further control of polysulfide chain length.
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Page/Page column 10-12
(2008/12/05)
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- PROCESS FOR PRODUCING DIALLYL DISULFIDE
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The invention provides a process for forming diallyl disulfide. The process comprises A) mixing together sulfur and at least one alkali metal sulfide in an initial aqueous medium in which at least about 90 volume percent of said aqueous medium is water, such that a disulfide source is formed in said initial aqueous medium thereby forming a disulfide source-conatining aqueous medium, and B) mixing together at least a portion of said disulfide source-containing aqueous medium and at lease one allyl halide selected from allyl cloride, allyl bromide, or a mixture of any two or all three of these, in the absence of any additional solvent other than water, at a temperature in the range of about 40?C to about 60?C, such that diallyl disulfide is formed.
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Page/Page column 12-16
(2010/10/20)
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- Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole
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A new synthesis of unsymmetrical disulfides is described. The reaction of a thiol R1SH with 1-chlorobenzotriazole (BtCl) at -78 °C in DCM affords a high-yielding conversion to R1SBt without appreciable formation of the symmetrical disulfide R1SSR1. R1SBt is then reacted with R2SH to form the unsymmetrical disulfide in a one-pot sequence with green character that avoids the use of toxic and harsh oxidizing agents. The methodology has been developed for synthesis of various types of disulfides.
- Hunter, Roger,Caira, Mino,Stellenboom, Nashia
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p. 8268 - 8271
(2007/10/03)
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- Medicinal products incorporating bound organosulfur groups
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Nutraceutical and dietary supplement formulations for delivering bioavailable thiols to a host, comprising certain organosulfur radicals, such as the allyl mercapto radical, bound to larger molecules such as proteins, resulting in the formation in the host's body of various allium-related compounds such as allicin. The formulations are produced by treating an ingestible material comprising a cysteine-containing protein with a thiol, disulfide, mixed disulfide, thiosufinate or mixed thiosulfinate so as to cause thiol residues to become disulfide bonded to cysteines contained in the protein.
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Page/Page column 22; 23; Sheet 4
(2008/06/13)
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- Nitric Acid Mediated Oxidative Transformation of Thiols to Disulfides
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Oxidation of thiols to disulfides are reported using nitric acid/methylene chloride. Environmentally benign, economically convenient and simple reaction condition represents an attractive alternative to the existing approaches on both the laboratory and the industrial scale.
- Misra, Anup Kumar,Agnihotri, Geetanjali
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p. 1079 - 1085
(2007/10/03)
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- Method for preparing aromatic diphenyl thioethers
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The invention concerns a method for preparing aromatic diphenyl thioethers. More particularly the invention concerns the preparation of 4-chloro-4′-thiomethyldiphenylether. The inventive method for preparing an aromatic diphenyl thioether is characterised in that it consists in reacting in an aqueous medium a diazonium salt of an aromatic diphenyl compound with a disulphide sulphur compound, in the presence of an efficient amount of a coupling catalyst.
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- Tetrabutylammonium peroxydisulfate in organic synthesis. XII. A convenient and practical procedure for the selective oxidation of thiols to disulfides with tetrabutylammonium peroxydisulfate under solvent-free conditions
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An efficient method for the oxidative coupling of thiols to their corresponding disulfide by (n-Bu4N2)S2O8 in high yields under solvent-free conditions is described. The reaction was applicable to a variety of thiols with high chemoselectivity.
- Chen, Fen-Er,Lu, Yun-Wen,He, Yan-Ping,Luo, You-Fu,Yan, Ming-Guo
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p. 3487 - 3492
(2007/10/03)
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- A rapid and efficient synthesis of symmetrical disulfides under microwave irradiation conditions
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A rapid and general method for the synthesis of symmetrical disulfides involves reaction of sulfur with sodium hydroxide under PTC-microwave irradiation condition to give sodium disulfide, which reacts with alkyl halides to afford the disulfides in good to excellent isolated yields.
- Wang, Jin-Xian,Gao, Lijuan,Huang, Danfeng
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p. 963 - 969
(2007/10/03)
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- Reduction of sulfur with borohydride exchange resin in methanol: Application to rapid and selective synthesis of disulfides
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A convenient and rapid method for the synthesis of symmetrical disulfides from alkyl or aryl alkyl halides using sulfurated borohydride exchange resin (SBER) under anhydrous conditions is described. Selective transfer of sulfur to an alkyl group rather than an aryl group is achieved using this methodology.
- Bandgar,Uppalla,Sadavarte
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p. 6741 - 6743
(2007/10/03)
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- S-nitrosothiol and disulfide formation through peroxynitrite-promoted oxidation of thiols
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Peroxynitrite reacts with thiols 1 at acidic pH to give the corresponding S-nitrosothiols 2 and disulfides 3. The formation of nitrosothiols 2, the yield of which is strongly pH-dependent, can be rationalized in terms of acid-catalyzed decomposition of the undissociated HPN, probably through the intermediacy of the protonated form H2PN+, leading to a species, X-NO, capable of nitrosating the thiol function. In contrast, the formation of disulfides 3 occurs in a manner independent of the pH, without the intermediacy of sulfanyl radicals. Under basic conditions, the peroxynitrite anion (PN) oxidizes the thiolate ion to sulfanyl radicals, eventually leading to disulfide 3, or undergoes a thiol-catalyzed decomposition. The former is the exclusive reaction exhibited by peroxynitrite at pH > 13.
- Grossi, Loris,Montevecchi, Pier Carlo,Strazzari, Samantha
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p. 131 - 135
(2007/10/03)
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- Reactions of 2-allylthiobenzimidazole, -oxazole, -thiazole, and the isomeric thiones with dichlorocarbene
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The reactions of 2-allylthiobenzimidazole, -oxazole, and -thiazole, and the thiones formed from them on heating, with dichlorocarbene have been investigated under phase transfer catalysis conditions.
- Ramazanova,Tarakanova,Vagabov,Litvinova,Anisimov
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p. 201 - 206
(2007/10/03)
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- Oxidation in fluoro alcohols: Mild and efficient preparation of disulfides from thiols
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Quantitative oxidative conversion of thiols to disulfides was effected by aqueous 30% H2O2 in trifluoroethanol at ambient temperature under neutral conditions.
- Kesavan, Venkitasamy,Bonnet-Delpon, Daniele,Begue, Jean-Pierre
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p. 223 - 225
(2007/10/03)
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- Thermal Degradation of Allyl Isothiocyanate in Aqueous Solution
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Allyl isothiocyanate in an aqueous solution was heated and refluxed at 100 °C for 1 h. The reaction mixtures were then extracted with methylene chloride and analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The mixtures in aqueous phase were analyzed by high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS) equipped with an atmospheric-pressure chemical ionization (APCI) interface. The compounds identified in the methylene chloride extracts included diallyl sulfide, diallyl disulfide, diallyl trisulfide, diallyl tetrasulfide, allyl thiocyanate, 3H-1,2-dithiolene, 2-vinyl-4H-1,3-dithiin, 4H-1,2,3-trithiin, and 5-methyl-1,2,3,4-tetrathiane. N,N′-Diallylthiourea, which was the major degradation product in the aqueous phase from the thermal reaction of allyl isothiocyanate, was identified by using LC-MS (APCI+), direct-probe EI-MS, and 1H-NMR. The possible mechanism for the formation of these products was proposed.
- Chen, Chung-Wen,Ho, Chi-Tang
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p. 220 - 223
(2007/10/03)
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- Preparation of dialkyl disulfides via reduction of alkylthiocyanates with TiCl4/Sm system
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Dialkyl disulfides can be readily prepared in moderate to good yields via reduction of alkylthiocyanates with TiCl4/Sm system in THF at 0°C.
- Guo, Hongyun,Zhan, Zhuangping,Zhang, Yongmin
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p. 2721 - 2724
(2007/10/03)
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- Use of a sacriflcial-sulfur electrode in electroorganic chemistry. V. Formation of the sequence CSSSC from S and thiols or thiolates
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At a working potential of about +2.0 V (vs SCE) the carbon-sulfur electrode is a source of the electrogenerated cation S2+. In organic media, this electrophile reacts with thiols (or thiolates) to give a mixture of polysulfides of which the trisulfide is the main product. The reaction between electrogenerated Sy2- and alkyl halides is less selective. Elsevier,.
- Do, Quang Tho,Elothmani, Driss,Simonet, Jacques,Guillanton, Georges Le
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p. 273 - 281
(2007/10/03)
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- A facile method for the syntheses of dialkyl disulfides from sulfur under phase transfer conditions
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A convenient reaction of alkyl halides with sulfur in alkaline medium has been found to afford disulfides in good to excellent isolated yield under phase transfer conditions.
- Wang,Cui,Hu
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p. 3573 - 3581
(2007/10/03)
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- B12 Mimicry in a Weak Ligand Environment: Oxidation and Alkylation of Thiols
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The first examples of alkylation and oxidation of thiols by cobalt in weakly coordinating ligand (MeCN) environments is presented as a mimic to B12-dependent nonenzymatic reaction.
- Chowdhury, Shantanu,Samuel, Purnima M.,Das, Indira,Roy, Sujit
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p. 1993 - 1994
(2007/10/02)
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- REACTION OF PYRROLES WITH CARBON DISULFIDE IN KOH/DMSO SYSTEM
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By the interaction of pyrroles with carbon disulfide and haloalkanes in a KOH/DMSO system, esters of 1- and 2-pyrrolyldithiocarboxylic acids have been synthesized.The influence of substituents on the direction of the reaction has been established.
- Trofimov, B. A.,Sobenina, L. N.,Mikhaleva, A. I.,Sergeeva, M. P.,Golovanova, N. I.,et al.
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p. 990 - 994
(2007/10/02)
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- SYNTHESIS OF DIALLYL DISULFIDE UNDER THE CONDITIONS OF PHASE-TRANSFER CATALYSIS
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The optimum conditions were found for the selective synthesis of diallyl disulfide with yields of 80-86percent by the reaction of allyl halides with sodium disulfide in the presence of quaternary ammonium salts.
- Nosyreva, V. V.,Amosova, S. V.
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p. 1218 - 1221
(2007/10/02)
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- Novel Alkylation with Tetrathiotungstates and Tetrathiomolybdates: Facile Synthesis of Disulfides from Alkyl Halides
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A novel reaction of alkyl halides with piperidinium tetrathiotungstate or piperidinium tetrathiomolybdate (MS42-) has been found to afford disulfides in good to excellent isolated yields under very mild reaction conditions.
- Dhar, Preeti,Chandrasekaran, Srinivasan
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p. 2998 - 3000
(2007/10/02)
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- Process for the production of isosolanone and solanone, intermediates useful in said process and organoleptic uses of said intermediates
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Described is a novel genus of compounds defined according to the structure: STR1 wherein Z represents hydrogen, MgX and the moiety having the structure: STR2 and X represents chlor, bromo, or iodo; as well as 5-isopropyl-8-methyl-5,8-nonadien-2-one; uses of same as intermediates in a process for producing isosolanone and solanone; and organoleptic uses of 5-isopropyl-8-methyl-5,8-nonadien-2-one and 2,6-dimethyl-5-methylene-1-hepten-4-ol. The novel process of our invention involved the steps of: (i) formation of the compound having the structure: STR3 by means of reacting 3-methyl-2-methylenebutanal with the compound having the structure: STR4 (ii) acid hydrolysis of the resulting compound in order to form 2,6-dimethyl-5-methylene-1-heptene-4-ol; (iii) reaction of 2,6-dimethyl-5-methylene-1-hepten-4-ol with methyl aceto acetate in order to form 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate or, directly, 5-isopropyl-8-methyl-5,8-nonadiene-2-one; (iv) reacting 2,6-dimethyl-5-methylene-1-hepten-4-yl aceto acetate in the presence of an appropriate catalyst to form the 5-isopropyl-8-methyl-5,8-nonadiene-2-one; and (v) isomerizing the 5-isopropyl-8-methyl-5,8-nonadien-2-one in order to form a mixture of solanone and the isosolanone or 5-isopropyl-8-methyl-5,8-nonadiene-2-one.
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- Synthesis of Unsymmetrical Functionalised Organic Sulphides
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Acyclic thioiminium salts and the condensed thiazolium salts in the presence of aqueous sodium hydroxide as such or under base catalyzed phase transfer catalysis conditions react with appropiate organic halides to provide corresponding unsymmetrical functionalized organic sulphides.With aqueous sodium hydroxide, thioiminium salts provide the disulphides corresponding to incipient thiol.
- Singh, Harjit,Batra, Manohar S.,Singh, Paramjit
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p. 131 - 136
(2007/10/02)
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- (E,Z)-Ajoene: A potent antithrombotic agent from garlic
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A report is presented of the structural characterization and simple synthesis of (E,Z)-ajoene.
- Block,Ahmad,Jain,et al.
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p. 8295 - 8296
(2007/10/02)
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- POLYMER SUPPORTED REAGENTS. THE USE OF ANION-EXCHANGERS IN THE SYNTHESIS OF SULPHIDES AND DISULPHIDES
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The macroreticular anion-exchanger Amberlyst A-26, in thiolate and disulphide form, reacts under mild conditions, with primary and secondary alkyl halides and tosylates to give good yields of sulphides and disulphides, respectively.The reaction seems to be of general applicability and is particularly useful in the synthesis of disulphides as no thiol is needed as starting material.The exhausted polymeric reagent is easily regenerable.
- Cainelli, Gianfranco,Contento, Michele,Manescalchi, Francesco,Plessi, Laura
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p. 461 - 464
(2007/10/02)
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