222713-05-5Relevant articles and documents
A new entry for the preparation of substituted aromatic carbonyl compounds mediated by Samarium(II) iodide
Yoda, Hidemi,Kohata, Naoki,Takabe, Kunihiko
, p. 1087 - 1094 (2003)
A new route to substituted aromatic lactones and lactams via SMI2-promoted desulfurization is described. Direct replacement of the phenylthio substituent by hydroxyalkylated groups featuring the novel accessible process for the construction of continuous quaternary carbon centers could be accomplished when the same type of reactions was undertaken with carbonyl compounds in the presence of SmI2.
Bifurcated synthesis of methylene-lactone- And methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams
Iijima, Ayumi,Inuzuka, Toshiyasu,Makino, Koki,Sengoku, Tetsuya,Yoda, Hidemi
supporting information, p. 2769 - 2775 (2020/12/11)
New synthetic methods for spirolactams bearing an α-methylene-γ-butyrolactone or its analogous methylene-lactam have been developed. The allylation of γ-phenylthio-functionalized γ-lactams with 2-(acetoxy)methyl acrylamides was accomplished by using 2.5 equivalents of NaH to give the corresponding adducts in excellent yields. The remaining phenylthio group was substituted with a hydroxy group by treatment with CuBr, and the resulting γ-hydroxyamides were cyclized under acidic conditions to afford the corresponding methylene-lactam-fused spirolactams in high yields. On the other hand, methylene-lactone-fused spirolactams could be delivered from the allyl adducts in high yields through a sequential N-Boc protection/desulfinative lactonization.
SmI2-promoted tandem desulfurization and reductive coupling reactions of aromatic lactams with carbonyl compounds
Yoda, Hidemi,Ujihara, Yasuaki,Takabe, Kunihiko
, p. 9225 - 9228 (2007/10/03)
Treatment of sulfur-substituted aromatic lactams with carbonyl compounds in the presence of samarium(II) diiodide was found to undergo novel tandem desulfurization and reductive coupling reactions to generate α-hydroxyalkylated lactams in high yield. Ster