17835-44-8Relevant academic research and scientific papers
Iron-Catalyzed One-Step Synthesis of Isothiazolone/1,2-Selenazolone Derivatives via [3+1+1] Annulation of Cyclopropenones, Anilines, and Elemental Chalcogens
Wang, Hongchen,Yan, Rulong
, p. 715 - 719 (2021/12/22)
Described herein is the one-step synthesis of isothiazolone/1,2-selenazolone derivatives via [3+1+1] cycloaddition of cyclopropenone derivatives, anilines, and elemental chalcogens. The cascade reaction involves the C?S, C?N, and N?S bond formation along with the cleavage of C?C bond. Both anilines and cyclopropenones are tolerated and give the corresponding products in 28–73% yields. (Figure presented.).
Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments
Sánchez García, Jessica J.,Joo-Cisneros, Rene S.,García-Bassoco, David,Flores-Alamo, Marcos,Stivalet, José M. Méndez,García-Valdés, Jesús,Klimova, Elena I.
, (2021/05/17)
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
Wu, Jian,Gao, Wen-Xia,Huang, Xiao-Bo,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
supporting information, p. 5555 - 5560 (2020/07/30)
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
Formation of 2,5-diaryl-1,3-dithiolylium-4-olate in thermal reaction of 4-aryl-1,3,2-oxathiazolylium-5-olate
Tono, Masaki,Aoto, Hiroshi,Matsudaira, Yorimasa,Sugiyama, Tom,Kajitani, Masatsugu,Akiyama, Takeo,Sugimori, Akira
, p. 4023 - 4026 (2007/10/02)
The reflux of a meso-ionic compound, 4-aryl-1,3,2-oxathiazolylium-5-olate (1), in toluene, chlorobenzene, or xylene gives another meso-ionic compound, 2,5-diaryl-1,3-dithiolylium-4-olate (2), by a radical mechanism.
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
Behringer, Hans,Meinetsberger, Eike
, p. 315 - 341 (2007/10/02)
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.
Photochemical and Thermal Reactions of Heterocycles. Part 3. Photoisomerisation, Photofragmentation, and Photodimerisation of Mesoionic 1,3-Dithiol-4-one and -4-imine Derivatives
Kato, Hiroshi,Shiba, Toshie,Aoki, Nobuo,Iijima, Hiroko,Tezuka, Hiroshi
, p. 1885 - 1890 (2007/10/02)
Photolysis of the mesoionic 2,5-diphenyl-1,3-dithiol-4-one (7) gave tetraphenyl-1,4-dithiin, tetraphenylthiophen, diphenylacetylene, and sulphur via the corresponding dimer (11) and 4,5-diphenyl-1,2-dithiol-3-one (12) which were isolable under appropriate conditions.Photolysis of the mesoionic N-benzoyl-2-phenyl-1,3-dithiol-4-imines (14) afforded the corresponding 1,2-dithiol-3-imines (15).The photochemical paths of the mesoionic dithiole systems are discussed in the light of the experimental results.
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
Behringer, Hans,Meinetsberger, Eike
, p. 1729 - 1750 (2007/10/02)
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.
