- Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones
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A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.
- Dar'In, Dmitry,Kantin, Grigory,Bakulina, Olga,Krasavin, Mikhail
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p. 2259 - 2266
(2020/08/26)
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- α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines
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The readily available α-diazo-β-oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5-fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3-triazoles. Excluding the Lewis acid promoter resulted in a clean and high-yielding formation of α-sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.
- Safrygin, Alexander,Dar'in, Dmitry,Kantin, Grigory,Krasavin, Mikhail
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supporting information
p. 4721 - 4724
(2019/08/01)
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- METHOD FOR PRODUCING PYRIDAZINONE COMPOUNDS AND INTERMEDIATE THEREOF
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The present invention relates to a novel method for producing a pyridazinone compound and an intermediate thereof as shown in the following scheme: wherein the symbols are as defined in the specification.
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Page/Page column 250-251
(2012/03/27)
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- Tetra-(tetraalkylammonium)octamolybdate catalysts for selective oxidation of sulfides to sulfoxides with hydrogen peroxide
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Tetra-(tetraalkylammonium)octamolybdate catalysts are successfully applied in the selective oxidation of various sulfides to sulfoxides with 30% aqueous hydrogen peroxide as oxidant under mild reaction conditions in 94-100% yield and 95-100% selectivity. The octamolybdate catalysts show high catalytic activity in a high ratio of substrate to catalyst (up to 10000:1) and are recyclable, with actively functional groups, including hydroxyl group and CC bonds, tolerated in the oxidation. The Royal Society of Chemistry 2009.
- Yang, Chuanbo,Jin, Qingping,Zhang, Hua,Liao, Jian,Zhu, Jin,Yu, Bin,Deng, Jingen
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supporting information; experimental part
p. 1401 - 1405
(2010/05/02)
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- Multicomponent cyclocondensations of β-ketosulfones with aldehydes and aminoazole building blocks
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The multicomponent reaction of methylsulfonylacetone (or α-methylsulfonylacetophenone) with aromatic aldehydes and aminoazoles (or urea) under microwave irradiation to yield 5,8-dihydroimidazolo[1,2-a]pyrimidines and 4,7-dihydro[1,2,4]triazolo[l,5-a]pyrimidines was studied. The influence of the type of aminoazole building block on the reactivity was established. In addition, an unusual reaction pathway for the Biginelli-type condensation of methylsulfonylacetone with aldehydes and urea leading to non-classical Hantzsch-type dihydropyridines was found.
- Gladkov, Eugene S.,Chebanov, Valentin A.,Desenko, Sergey M.,Shishkin, Oleg V.,Shishkina, Svetlana V.,Dallinger, Doris,Kappe, C. Oliver
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experimental part
p. 469 - 480
(2009/09/08)
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- Facile polyethylene glycol (PEG-400) promoted synthesis of β-ketosulfones
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An efficient and convenient synthesis of β-ketosulfones is described. Reaction of an α-haloketone with sodium alkyl/aryl sulphinate yields the corresponding β-ketosulfone promoted by polyethylene glycol (PEG-400) as an efficient reaction medium.
- Suryakiran,Reddy, T. Srikanth,Ashalatha,Lakshman,Venkateswarlu
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p. 3853 - 3856
(2007/10/03)
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- PREFERRED CONFORMATIONS OF METHYLTHIO-ACETONE AND -ACETOPHENONE, METHYLSULPHONYL-ACETONE AND -ACETOPHENONE, FROM MOLECULAR-MECHANICS AND DIPOLE-MOMENT TECHNIQUES
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Preferred conformations for the title compounds are determined from calculated molecular-mechanics energies in the gaseous phase and analysis of the dipole moments measured in solvents of low dielectric permittivity.In all cases, the gauche conformer having the Me-S bond situated far away from the Me(-C) (or Ph(-C)) group, and nearly bisecting one of the C(=O)-C-H valleys, is predominant.
- Lumbroso, H.,Bertin, D. M.,Olivato, P. R.,Bonfada, E.,Mondino, M. G.,Hase, Y.
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p. 113 - 122
(2007/10/02)
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