Self-modulated highly chemoselective direct-reductive-amination (DRA) of benzaldehydes straightforward to N-monosubstituted benzylamine hydrochlorides
摘要:
All unprecedented efficient and chemoselective DRA of benzaldehydes and primary amines was developed to directly yield N-monosubstituted benzylamine hydrochlorides as single products in practically quantitative yields. The method was characterized by simply adding a few milliliters of CHCl3 in the conventional Pd-C catalytic hydrogenation system at atmospheric pressure and room temperature. A self-modulated system and a four-stage cyclic pathway were proposed. (C) 2008 Elsevier Ltd. All rights reserved.
A short route to cis-5-(2-nitrophenyl)-2-azabicyclo[3.3.0]octanes involving ozonolysis of 2-allyl-2-(2-nitrophenyl)-1,3-cyclopentanedione followed by double reductive amination is described. The preferred conformations of the azabicyclic ringsystem in these compounds are reported.
3a-(o-Nitrophenyl)octahydroindol-4-ones: Synthesis and spectroscopic analysis
作者:Daniel Solé、Joan Bosch、Josep Bonjoch
DOI:10.1016/s0040-4020(96)00065-8
日期:1996.3
A short entry to 3a-(o-nitrophenyl)octahydroindol-4-ones employing ozonolysis and double reductive amination of 2-allyl-2-(o-nitrophenyl)-1,3-cyclohexanedione (9) is described. The symmetric dione 9 is synthesized in a 50% overall yield from 1,3-cyclohexanedione by means of o-nitroarylation followed by O-allylation and subsequent Claisen rearrangement. Configurational and conformational aspects of azabicyclic derivatives 1 (a-k) are discussed.