103675-99-6Relevant articles and documents
Copper-Catalyzed Aza-Sonogashira Cross-Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles
Lavernhe, Rémi,Torres-Ochoa, Rubén O.,Wang, Qian,Zhu, Jieping
supporting information, p. 24028 - 24033 (2021/10/07)
Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.
The Neber route to substituted indoles
Taber, Douglass F.,Tian, Weiwei
, p. 1058 - 1059 (2007/10/03)
Two complementary procedures have been developed for the conversion of the oximes of α-aryl ketones to azirines. On heating, the azirines rearrange smoothly to the corresponding indoles. The overall transformation offers a versatile route to indoles, complementary to the Fischer indole synthesis. Copyright
The Palladium Assisted Transfer Reduction of α,β-Unsaturated Nitroalkenes to Oximes Using Ammonium Formate
Kabalka, George W.,Pace, R. David,Wadgaonkar, P.P.
, p. 2453 - 2458 (2007/10/02)
α,β-Unsaturated nitroalkenes are readily reduced to the corresponding oximes in good yields using ammonium formate in the presence of palladium.The reactions occur rapidly at room temperature in a solvent system of methanol and tetrahydrofuran.
THE PALLADIUM ASSISTED TRANSFER REDUCTION OF α,β-UNSATURATED NITROALKENES USING SODIUM HYPOPHOSPHITE: A SYNTHESIS OF OXIMES
Varma, Rajender S.,Varma, Manju,Kabalka, George W.
, p. 91 - 96 (2007/10/02)
α,β-Unsaturated nitroalkenes are readily reduced by sodium hypophosphite to the corresponding oximes in the presence of palladium.
A FACILE KETOXIME PREPARATION VIA THE REDUCTION OF Αa,β-UNSATURATED NITROALKENES USING SODIUM STANNITE
Varma, Rajender S.,Varma, Manju,Kabalka, George W.
, p. 6013 - 6014 (2007/10/02)
α,β-Unsaturated nitroalkenes are readily reduced by sodium stannite to ketoximes at room temperature.