16.
Abstract
The compound
5, containing the novel heterocycle 2-oxa-4,7-diazabicyclo[3.3.1]non-3-ene, has been obtained in a synthetic approach toward
oxazoles and 1,3-diazepanes of natural product-like complexity from cyclization and rearrangement of δ-lactam cyanamides.
When this procedure was applied to a silyl-protected
N-((
3S,
4S,
5S)-4,5-dihydroxy-2-oxopiperidin-3-yl)cyanamide (
2b) formation of the novel heterobicyclic scaffold
5 was observed along with the expected oxazole (
3b) and diazepane (
4b) products. The crystal structures of
5 and diazepane
4b are described. Compound
5 crystallized from methanol in the monoclinic system, P2
1 space group with unit cell parameters
a = 15.3402(9),
b = 7.2717(4),
c = 22.5803(13),
β = 106.8620(10) and a cell volume of 2410.5(2) A
3.
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