4440-99-7Relevant articles and documents
A green and practical one-pot two-step strategy for the synthesis of symmetric 3,6-diarylpyridazines
Rimaz, Mehdi,Mousavi, Hossein,Khalili, Behzad,Aali, Farkhondeh
, p. 1389 - 1397 (2018/11/26)
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.
Base- and metal-free decarboxylative aldol reaction of β-ketoacids with glyoxylate hydrates and glyoxal monohydrates in water
Ren, Nan,Nie, Jing,Ma, Jun-An
, p. 6609 - 6617 (2018/06/08)
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.
A novel coupling reaction of α-halo ketones promoted by SmI3/CuI
Liu, Yongjun,Zhao, Hengmin,Tian, Guang,Du, Feng,Qi, Yan,Wen, Yonghong
, p. 26317 - 26322 (2016/03/25)
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.
Reductive ring-opening reaction of 2,3-epoxy-1,4-butanediones with SbCl3-Bu4NI in the presence of Na2S 2O3·5H2O
Sayama, Shinsei
, p. 2115 - 2124 (2007/10/03)
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.
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
Hasegawa,Chiba,Nakajima,Suzuki,Yoneoka,Iwaya
, p. 1248 - 1252 (2007/10/03)
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.
Reductive transformation of α β-epoxy ketones and other compounds promoted through photoinduced electron transfer processes with 1,3-dimethyl- 2-phenylbenzimidazoline (DMPBI)
Hasegawa, Eietsu,Yoneoka, Akira,Suzuki, Kumiko,Kato, Teru,Kitazume, Takashi,Yanagi, Kazuhiro
, p. 12957 - 12968 (2007/10/03)
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.
STANNOUS (II) TRIFLATE PROMOTED REARRANGEMENT OF β-KETO SULFOXIDES. SYNTHESIS OF 1,4-DIKETONES
Shimizu, Makoto,Akiyama, Takahiko,Mukaiyama, Teruaki
, p. 1531 - 1534 (2007/10/02)
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.
