Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 20, Pages 6927-6930Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo049396d
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The synthesis and chemical reactivity of pyridazinedione-based enediynes (1, 2) are described. Both of these enediynes, namely the dihydro compound 1 and its corresponding tetrahydro analogue 2, were prepared by double N,O-alkylation of the corresponding heterocyclic system with the acyclic enediynyl dibromide 8 in good yields. Their single-crystal X-ray structures revealed similar c, d distances (distance between the acetylenic carbons undergoing covalent connection in Bergman cyclization). Interestingly, these molecules undergo Bergman cyclization at different rates, and the reactivity is shown to be dependent upon the state of hybridization of C-4 and C-5 atoms of the parent heterocyclic ring.
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