Proton magnetic resonance studies of compounds with bridgehead nitrogen atoms—XIX Configurational and conformational studies with derivatives of hexahydropyrido [2,1‐c][1,4]oxazin‐4(3H)‐ones
- 1 April 1972
- journal article
- research article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 4 (2) , 283-308
- https://doi.org/10.1002/mrc.1270040209
Abstract
A series of substituted hexahydropyrido [2,1‐c][1,4]oxazin‐4(3H)‐ones has been prepared by reaction of the sodio derivative of the appropriate piperidyl carbinol with ethyl chloroacetate. From a study of their NMR spectra the configurations of these compounds have been assigned and the conformation of the perhydro‐1, 4‐oxazinone moiety shown to be that with the ring oxygen atom and the angular hydrogen on the same side of the plane defined by C3C(O)N. The synthesis and NMR spectra of hexahydro‐2H‐pyrido [1,2‐d][1,4]oxazepin‐5(4H)‐one, 1,6,11,11a‐tetrahydro [1,4]‐oxazino [4,3‐b]isoquinolin‐4(3H)‐one and of hexahydropyrido [2,1‐c][1,4]thiazin‐4(3H)‐one are also discussed. cis‐6,9a‐H‐6‐Methyl‐hexahydropyrido[2,1‐c][1,4]oxazin‐4(3H)‐one is shown to exist in a conformation containing a deformed perhydropyridine ring.Keywords
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