91760-13-3Relevant academic research and scientific papers
Hydride Transfer from Iron(II) Hydride Compounds to NAD(P)+ Analogues
Zhang, Fanjun,Jia, Jiong,Dong, Shuli,Wang, Wenguang,Tung, Chen-Ho
, p. 1151 - 1159 (2016/06/01)
Iron(II) hydride complexes of the "piano-stool" type, Cp?(P-P)FeH (P-P = dppe (1H), dppbz (2H), dppm (3H), dcpe (4H)) were examined as hydride donors in the reduction of N-benzylpyridinium and acridinium salts. Two pathways of hydride transfer, "single-step H-" transfer to pyridinium and a "two-step (e-/H?)" transfer for acridinium reduction, were observed. When 1-benzylnicotinamide cation (BNA+) was used as an H- acceptor, kinetic studies suggested that BNA+ was reduced at the C6 position, affording 1,6-BNAH, which can be converted to the more thermally stable 1,4-product. The rate constant k of H- transfer was very sensitive to the bite angle of P-Fe-P in Cp?(P-P)FeH and ranged from 3.23 × 10-3 M-1 s-1 for dppe to 1.74 × 10-1 M-1 s-1 for dppm. The results obtained from reduction of a range of N-benzylpyridinium derivatives suggest that H- transfer is more likely to be charge controlled. In the reduction of 10-methylacridinium ion (Acr+), the reaction was initiated by an e- transfer (ET) process and then followed by rapid disproportionation reactions to produce Acr2 dimer and release of H2. To achieve H? transfer after ET from [Cp?(P-P)FeH]+ to acridine radicals, the bulkier acridinium salt 9-phenyl-10-methylacridinium (PhAcr+) was selected as an acceptor. More evidence for this "two-step (e-/H?)" process was derived from the characterization of PhAcr? and [4H]+ radicals by EPR spectra and by the crystallographic structure confirmation of [4H]+. Our mechanistic understanding of fundamental H- transfer from iron(II) hydrides to NAD+ analogues provides insight into establishing attractive bio-organometallic transformation cycles driven by iron catalysis.
A Synthesis of N-Acyl-1,2-dihydropyridines
Wyle, Michael J.,Fowler, Frank W.
, p. 4025 - 4029 (2007/10/02)
A new approach to the synthesis of N-acyl-1,2-dihydropyridines based on the cyclization of N-acyl-1-azatrienes is introduced.These latter compounds were not isolated but were produced in the gas phase as transient intermediates by the flash vacuum pyrolysis of O-methoxycarbonyl N-penta-1,3-dien-5-yl hydroxamic acid derivatives 8.
