- A green and practical one-pot two-step strategy for the synthesis of symmetric 3,6-diarylpyridazines
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A simple, mild, and efficient synthesis of symmetric 3,6-diarylpyridazine derivatives using a green catalytic one-pot two-step reaction of aryl methyl ketones, arylglyoxal monohydrates, and hydrazine hydrate was developed. Environmentally benign nature, high atom-economy, no harmful byproduct, easy workup procedure, no column chromatography steps, and moderate to excellent yields of the products are the salient features of this new multicomponent-based methodology.
- Rimaz, Mehdi,Mousavi, Hossein,Khalili, Behzad,Aali, Farkhondeh
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p. 1389 - 1397
(2018/11/26)
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- Base- and metal-free decarboxylative aldol reaction of β-ketoacids with glyoxylate hydrates and glyoxal monohydrates in water
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An environmentally benign decarboxylative aldol reaction of β-ketoacids with glyoxylate and glyoxal monohydrates in water is reported. The reaction proceeds smoothly without any base and metal catalysts, affording the corresponding β-hydroxy ketones in high yields. A preliminary mechanism study of this aldol transformation suggests a stepwise process involving the nucleophilic addition of β-ketoacids to glyoxylate hydrates and glyoxal monohydrates followed by a subsequent decarboxylation reaction.
- Ren, Nan,Nie, Jing,Ma, Jun-An
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p. 6609 - 6617
(2018/06/08)
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- A novel coupling reaction of α-halo ketones promoted by SmI3/CuI
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With SmI3 as the Lewis acid and catalyzed by CuI in DMF, α-haloketones were transformed unexpectedly into α-hydroxy-1,4-diketones in good to moderate yields. The mechanism was probed and a plausible reaction pathway was proposed. DMF was assumed to play a dual role both as a hydroxyl source and as a solvent.
- Liu, Yongjun,Zhao, Hengmin,Tian, Guang,Du, Feng,Qi, Yan,Wen, Yonghong
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p. 26317 - 26322
(2016/03/25)
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- Reductive ring-opening reaction of 2,3-epoxy-1,4-butanediones with SbCl3-Bu4NI in the presence of Na2S 2O3·5H2O
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1,4-Disubstituted 2,3-epoxy-1,4-butanediones were converted to 1,4-disubstituted 2-hydroxy-1,4-butanediones with SbCl3-Bu 4NI in the presence of Na2S2O 3-5H2O. The ring opening of terminal epoxides can also be accomplished to afford the corresponding haloalcohol with SbCl3 and tetrabutylammonium halides, Bu4NX (X = Cl, Br, I) under the same reaction conditions. Copyright Taylor & Francis, Inc.
- Sayama, Shinsei
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p. 2115 - 2124
(2007/10/03)
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- 1,3-Dimethyl-2-phenylbenzimidazoline (DMPBI)-acetic acid: An effective reagent system for photoinduced reductive transformation of α,β-epoxy ketones to β-hydroxy ketones
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A combination of 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) and acetic acid has been utilized for photoinduced reductive transformation of α,β-epoxy ketones to β-hydroxy ketones. Study on photoreactions using several proton donors revealed that acetic acid is superior to other proton donors such as HCl, p-TsOH, MeOH, and water. 1,3-Dimethyl-2-phenylbenzimidazolium was produced in the reaction with acetic acid while N-benzoyl-N,N′-dimethyl-o-phenylenediamine was formed in aqueous solvents. When THF solutions containing aryl carbonyl possessing α,β-epoxy ketones and DMPBI and acetic acid were irradiated (λ > 280 nm), β-hydroxy ketones were isolated in good to excellent yields. Photosensitized conditions (λ > 340 nm) were employed for the reactions of alkyl carbonyl possessing α,β-epoxy ketones.
- Hasegawa,Chiba,Nakajima,Suzuki,Yoneoka,Iwaya
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p. 1248 - 1252
(2007/10/03)
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- Reductive transformation of α β-epoxy ketones and other compounds promoted through photoinduced electron transfer processes with 1,3-dimethyl- 2-phenylbenzimidazoline (DMPBI)
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Photoreactions of epoxy ketones, aromatic ketones, haloketones, and aromatic halides with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) were studied. Photoinduced single-electron transfer from DMPBI to such substrates initiates the reactions, followed by radical rearrangement and reduction to finally give several reduced products in modest to good yields.
- Hasegawa, Eietsu,Yoneoka, Akira,Suzuki, Kumiko,Kato, Teru,Kitazume, Takashi,Yanagi, Kazuhiro
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p. 12957 - 12968
(2007/10/03)
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- STANNOUS (II) TRIFLATE PROMOTED REARRANGEMENT OF β-KETO SULFOXIDES. SYNTHESIS OF 1,4-DIKETONES
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Stannous triflate promotes rearrangement of β-keto sulfoxides to generate α-thiocarbocation, which in turn react with silyl enol ethers to give 2-arylsulfenyl-1,4-diketones in good yields.
- Shimizu, Makoto,Akiyama, Takahiko,Mukaiyama, Teruaki
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p. 1531 - 1534
(2007/10/02)
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