5433-10-3Relevant articles and documents
Olefin Amine (OLA) Reagents for the Synthesis of Bridged Bicyclic and Spirocyclic Saturated N-Heterocycles by Catalytic Hydrogen Atom Transfer (HAT) Reactions
Wang, Ya-Yi,Bode, Jeffrey W.
supporting information, p. 9739 - 9745 (2019/06/17)
Spiro- and bridged bicyclic structures are in demand for their sp3-rich frameworks that offer unique physiochemical properties and precisely positioned substituent groups. In order to rapidly access such molecules in a cross-coupling fashion we describe olefin amine (OLA) reagents for the transformation of aldehydes and ketones into all three topological types of bicyclic N-heterocycles: bridged, spiro-, and fused rings. The OLA reagents are easily prepared and allow the synthesis of complex molecular frameworks under operationally simple conditions that tolerate a wide array of functional groups. Investigations into the Mn or Fe promoted reaction pathway support a metal hydride hydrogen atom transfer (MH-HAT) to generate a C-centered radical that undergoes addition to an unactivated imine, leading to an N-centered radical. A catalytic cycle featuring regeneration of the metal catalyst by O2 and a second HAT to form the unprotected saturated N-heterocycle appears to be operative.
Nano-tube TiO2 as a new catalyst for eco-friendly synthesis of imines in sunlight
Hosseini-Sarvari, Mona
experimental part, p. 547 - 550 (2012/01/06)
Nanomaterials are considered as suitable heterogeneous catalysts for many organic reactions. Herein nano-tube TiO2 has been reported as a heterogeneous catalyst, for synthesis of imines in sunlight at room temperature under solvent-free conditions. The condensation of less electrophilic carbonyl compounds with poorly nucleophilic amines was afforded imines in excellent yields.
SIMPLE SYNTHESIS OF 3-(N-ALKYLAMINO)-1-PROPANOLS
Artyushin, O. I.,Petrovskii, P. V.,Mastryukova, T. A.,Kabachnik, M. I.
, p. 1911 - 1913 (2007/10/02)
Various 3-(N-alkylamino)-1-propanols were obtained by the lithium aluminum hydride reduction of the products of the reaction of 3-amino-1-propanol with carbonyl compounds.This method for the synthesis of aminopropanols is applicable in the case of optimal electrophilicity of the carbonyl component.