Synthesis and Crystal Structure of a Novel Heterocycle, 2-Oxa-4,7-Diazabicyclo[3.3.1]Non-3-Ene |
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| Authors: | Sanjay Dutta Sergey M Dibrov Bao T Ho Cody J Higginson Thomas Hermann |
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| Institution: | (1) Department of Chemistry and Biochemistry, University of California, 9500 Gilman Drive, San Diego, La Jolla, CA 92093, USA;(2) Present address: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA; |
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| Abstract: | Abstract The compound 5, containing the novel heterocycle 2-oxa-4,7-diazabicyclo3.3.1]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, P21 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) A3. |
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