13232-76-3

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 5781, 1973 DOI: 10.1021/ja00798a068

InChI:InChI=1/C15H10S3/c16-15-13(11-7-3-1-4-8-11)14(17-18-15)12-9-5-2-6-10-12/h1-10H

Upstream product

• 833-81-8 (E)-1,2-diphenylpropene 
• 2042-85-5 1,2-diphenylpropan-1-one 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 80158-70-9 4,5-Diphenyl-3H-1,2-dithiol-3-thion-S-oxid 
• 10269-25-7 4-methyl-5-phenyl-1,2-dithiole-3-thione 
• 2570-01-6 2,3-diphenylcyclopropen-1-thione 
• 19018-13-4 2-[4-(2-Oxo-1,2-diphenyl-ethylidene)-[1,3]dithietan-2-ylidene]-1,2-diphenyl-ethanone 
• 88406-86-4 2-Azido-4,5-diphenyl-[1,3]dithiole 
• 80158-72-1 3,3-Diiodo-4,5-diphenyl-3H-[1,2]dithiole 
• 80158-66-3 C₂₂H₁₇N₂O₂S₃^(1-)*Li⁽¹⁺⁾ 
• 55836-89-0 3,4-Diphenyl-1,2-dithiolylium-bromid 
• 17835-44-8 4,5-diphenyl-3H-1,2-dithiol-3-one 
• 43155-31-3 4,5-Diphenyl-3H-1,2-dithiol-3-on-tosylhydrazon 
• 532-11-6 anethole trithione 

Downstream Products

• 13232-77-4 3-(Methylthio)-4,5-diphenyl-1,2-dithiolium-iodid 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 81385-73-1 5,6-Bis(4-chlorphenyl)-2,3-diphenylthieno<3,2-b>furan 
• 81385-75-3 5,6-Bis-(4-chloro-phenyl)-2-[1,2-diphenyl-2-thioxo-eth-(E)-ylidene]-[1,3]dithiin-4-one 
• 81385-74-2 5,6-Bis-(4-chloro-phenyl)-2-[1,2-diphenyl-2-thioxo-eth-(Z)-ylidene]-[1,3]dithiin-4-one 
• 81385-76-4 4,5-bis(4-methoxyphenyl)-3H-1,2-dithiol-3-one 
• 81385-77-5 5,6-Bis(4-methoxyphenyl)-2,3-diphenylthieno<3,2-b>furan 
• 77654-98-9 (diethylamino-4 methyl-5 dithiole-1,3 ylidene-2)-2 diphenyl-1,2 ethanethione 
• 17835-44-8 4,5-diphenyl-3H-1,2-dithiol-3-one 
• 80608-91-9 2,3,5,6-Tetraphenylthieno<3,2-b>furan 
• 81385-51-5 2-[1,2-Diphenyl-2-thioxo-eth-(Z)-ylidene]-5,6-diphenyl-[1,3]dithiin-4-one 
• 81385-79-7 5-Methyl-2,3,6-triphenylthieno<3,2-b>furan 
• 35093-32-4 2,3,5,6-tetraphenylthieno[3,2-b]thiophene 
• 80158-70-9 4,5-Diphenyl-3H-1,2-dithiol-3-thion-S-oxid 

Relevant academic research and scientific papers

Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments

A new synthesis method was established for 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones, from different cyclopropenones: diphenyl (a), bis-(4-methoxyphenyl (b), diferrocenyl (c) and diruthenocenyl (d), in the presence of elemental sulfur with yields of the 5a-d (35–57%), or in the presence of the additive NaHS, with yields of the 5a-d (45–72%) and 6a-d (10–18%). The characterization of the new compounds was conducted by IR, 1H and 13C NMR spectroscopy, elemental analysis, mass-spectrometry. In addition, X-ray crystallographic analysis of the compounds 5a,b,d was conducted. The redox properties of the heterocyclic compounds were investigated using cyclic (CV), differential pulse (DPV) and square wave (SWV) voltammetries.

Selective [3 + 2] Cycloaddition of Cyclopropenone Derivatives and Elemental Chalcogens

A highly efficient method is disclosed for the synthesis of 1,2-dichalcogen heterocycles via [3 + 2] cycloaddition of cyclopropenone derivatives and elemental chalcogens. Different from other cyclopropenone derivatives, cyclopropenselenones undergo unprec

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Syntheses de bis(dithiole-1,2 et diselenole-1,2 ylidenes)-3,3' et de derives du dithietanne-1,3

The dimerisation of 3-chloro 1,2-dithiolylium and 1,2-diselenolylium ions with aryl substituents in the 5-position leads to the corresponding chalcogenafulvalenes.On the other hand the dimerisation of the 1,2-dithiole derivatives with the 5-methylthio sub

THERMOLYSIS OF 1,3-DITHIOL-2-YL AZIDES AND THERMAL PROPERTIES OF THE RESULTING 1,4,2-DITHIAZINES

2-Substituted 1,3-dithiol-2-yl azides, on thermolysis in refluxing toluene, give 3-substituted 1,4,2-dithiazines wich thermally extrude sulfur atom of the 4-position selectively to yield 3-substituted isothiazoles, while 2-unsubstituted 1,3-dithiol-2-yl azides undergo both ring expansion yielding 1,4,2-dithiazines and peculiar thermal dissociation into 1,3-dithiol-2-ylidene carbenes and hydrogen azide.

1,1',2,2'-Tetrathiafulvalenes, IV. - On the Reactions of Cyclopropen(thio)nes with 1,2-Dithiole Compounds: Thienothiophenes, Thienofurans, 4H-Furopyrroles, 1,2-Dithiole-3-(thi)ones, and other Heterocycles Containing Sulfur

4,5-Disubstituted 1,2-dithiole-3-thiones (1,2-trithiones) 1 react with 2,3-diphenylcyclopropenethione (2a) to give by elimination of two atoms sulfur thienothiophenes 5.The reaction of 1a with 2a yields in addition tetraphenylthieno-1,2-dithiin (6a). 1,2-Trithiones react with 2,3-diarylcyclopropenones 7 (R3=Aryl) to give the corresponding thienofurans 8 and 1,2-dithiole-3-ones 9. - In 4-position unsubstituted 5-aryl-1,2-trithiones and 2,3-diarylcyclopropenones 7 (R3=Aryl) react in a more complex manner.In the reaction of 4,5-disubstituted 3-phenylimino-1,2-dithiole-3-thiones 18 with 7 (R3=Aryl) 4H-Furopyrroles 19 are formed. - Furthermore it will be reported on conversions of 5-phenyl-3H-1,2,4-dithiazole-3-thione (24), 2-benzyl-4-methyl-3-phenyl-1,2-thiazole-5(2H)-thione (27a), and 2-benzyl-4-phenyl-1,2-thiazole-5(2H)-thione (27b) in the reactions with the cyclopropenones 7d respective 7a.

1,1',2,2'-Tetrathiafulvalenes, II. - Thienothiophenes from 1,2-Dithiole Compounds; 3H-1,2-Dithiol-3-ylidenes (1,2-Dithiole-3-carbenes) as Supposed Intermediates

3,3'-Bi(3H-1,2-dithiolylidenes) (1,1',2,2'-Tetrathiafulvalenes) 5 are not obtainable with the following reactions which, however, have proved to be a good approach to the corresponding 1,3-isomers 3: 1) Deprotonation of 1,2-dithiolylium cations 4, 2) pyrolysis of alkali derivatives from 1,2-dithiol-2-one tosylhydrazones 26 (Bamford-Stevens reaction), or 3) partial desulfuration of 1,2-dithiole-3-thiones 6 by means of trivalent phosphorus compounds.These reactions with the 1,2-isomers always yield thienothiophenes 8 accompanied by the related 1,2-dithiole-3-thiones 6 (1,2-trithiones) and in the case of 26 also by azines 27.Partial desulfuration of 1,2-trithiones 6 by copper bronze again yields the corresponding thienothiophenes 8 instead of 5.Thermal decomposition of the 1,2-dithiolylium iodide 34 or 34' yields the thienothiophene 8a together with the 1,2-trithione 6a.Surprisingly, the P4S10-sulfuration of "desaurines" 37 gives thienothiophenes again and also 1,2-dithiole-3-thiones 6. - 1-Morpholinocyclohexene (18) reacts with the 1,2-dithiolylium cation 4a (X = ClO4) to give a formal 1:1 adduct from the carbene 9a and the enamine for which the structure 19 is proposed.

1,1'2,2'-Tetrathiafulvalenes, III. - Syhthesis, Properties, and Reactions of 3,3'-Bi(3H-1,2-dithiolylidenes)(1,1',2,2'-Tetrathiafulvalenes)

1,1',2,2'-tetrathiafulvalenes 1 can be prepared by different methods from the cations of 1,2-dithiolylium salts 4 which are either unsubstituted or appropriate substituted in 3-position (instead of 3-Cl also H or SCH3).The structure of 1 is substantiated by chemical arguments.IR and 13C-NMR spectra support the absence of thioxo groups. - Like the 1,1',3,3'-isomers 2 the 1,1',2,2'-tetrathiafulvalenes are disposed to stepwise donation of electrons with formation of the radical cation and dication salts 25 or 11, respectively, as well as to the formation of charge transfer complexes with tetracyanoethylene, tetracyanoquinodimethane, and 2,3-dichloro-5,6-dicyanobenzoquinone.Tris(triphenylphosphine)rhodium(I) chloride and tetrakis(triphenylphosphine)platinum(O) yield complexes with 1a. - Thermolysis of 1 produces thienothiophenes 6.Partial desulfuration of 1a, for example, is also feasible with oxidizing agents like lead(IV) acetate.Selenium dioxide, however, gives the corresponding thienofuran 41.The reaction with trialkyl phosphites yields a disulfide - probably the 2,2'-bi(2H-thietylidene) 38 - the thermolysis of which gives the thienothiophene 6a. - Compounds 1a and 1c do not react with dimethyl acetylenedicarboxylate, isothiocyanate, several 1,3-dipoles (azides), and also not with elementary sulfur, however, 1e forms with sulfur the 3H-1,2-dithiol-3-thione 5e (X = S).