Synthesis and thermolysis of heterocyclic 3-aza-3-ene-1,5-diynes(1) |
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Authors: | Nadipuram Asha K David Wendi M Kumar Dalip Kerwin Sean M |
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Affiliation: | Division of Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, 78712, USA. |
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Abstract: | [reaction: see text] Simple, acyclic 3-aza-3-ene-1,5-diynes undergo an aza-Bergman rearrangement to a fleeting 2,5-didehydropyridine (2,5-ddp) intermediate that rapidly ring-opens to beta-alkynylacrylonitrile products. In an effort to access longer-lived 2,5-ddp intermediates, we have prepared heterocyclic 3-aza-3-ene-1,5-diynes. The thermolysis of one such heterocyclic aza-enediyne does not afford products derived from trapping a 2,5-ddp intermediate but rather cyclopropanes that appear to arise from a carbene intermediate and a product that appears to be a trapping product from a 2,3-ddp intermediate. |
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