697301-71-6Relevant articles and documents
Direct Enamido C(sp2)?H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates
Cao, Hao-Qiang,Liu, Hao-Nan,Liu, Zhe-Yuan,Ma, Jun-An,Qiao, Bao-Kun,Zhang, Fa-Guang
supporting information, p. 5515 - 5521 (2020/04/27)
Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2)?H diphosphorylation. This reaction represents a rare example of realizing the challenging double C?P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.
Synthesis of 2,3-Dihydro-1H-azepine and 1H-Azepin-2(3H)-one Derivatives from Intramolecular Condensation between Stable Tertiary Enamides and Aldehydes
Zhu, Wenju,Zhao, Liang,Wang, Mei-Xiang
, p. 12047 - 12057 (2016/01/09)
A new strategy to construct 2,3-dihydro-1H-azepine and 1H-azepin-2(3H)-one heterocyclic rings is reported based on emerging tertiary enamide synthons. Under very mild conditions employing BBr3 as a Lewis acid catalyst and P2O5 as an additive, tertiary enamides that contain a formyl group underwent highly efficient and scalable intramolecular cyclic condensation to afford diverse 2,3-dihydro-1H-azepine and 1H-azepin-2(3H)-one derivatives in 71-96% yields. The reaction proceeded most probably through a nucleophilic addition of enamides to aldehyde, deprotonation, and dehydration cascade. Application of the method in the synthesis of dihydro-azepino[2,1-a]isoindol-5-ones, the core structure of naturally occurring lennoxamine, was also demonstrated.
A mild and convenient synthesis of N-carbobenzyloxy ketimines
Matsuo, Jun-Ichi,Tanaki, Yumi,Kido, Aimi,Ishibashi, Hiroyuki
, p. 2896 - 2898 (2008/09/18)
N-Carbobenzyloxy (Cbz) ketimines were prepared conveniently from N-Cbz amines by oxidation with N-tert-butylbenzenesulfinimidoyl chloride. The Royal Society of Chemistry 2006.