95178-33-9Relevant academic research and scientific papers
Stereochemical Studies. Part 78. Saturated Heterocycles. Part 65. Synthesis and Spectroscopic Studies of cis-5,6-Trimethylene-, and cis- and trans-5,6-Tetra- and -Pentamethylene-1,3-oxazinan-4-ones
Fueloep, Ferenc,Bernath, Gabor,Sohar, Pal,Pelczer, Istvan
, p. 2043 - 2048 (2007/10/02)
N-Methyl-cis-5,6-trimethylene-, and cis- and trans-5,6-tetra- and -pentamethylene-1,3-oxazinan-4-one derivatives (15) and (16) were prepared by cyclisation, with aldehydes, of the appropriate alicyclic 2-hydroxy-1-carboxamides.In each case, formation of the new C-2 centre of chirality was found to take place stereospecifically and only the (r-5,t-2,t-6) and (r-5,c-2,c-6) diastereomers, respectively, were formed.The conformations of the N-methyl-and N-unsubstituted cis-trimethylene-, cis-tetramethylene-, and cis-pentamethylene-1,3-oxazinan-4-ones (13)-(16) were determined by 1H and 13C n.m.r. spectroscopy in solution.Good agreement was obtained with the earlier data established by X-ray diffraction analysis of the crystalline substances.The relative steric structure of the C-2 centre of chirality was also proved by d.n.O.e. measurements.It was found that the substituent at position 2 didnot affect the conformation significantly.
