Synthesis and Reactivity of Cinnoline-Fused Cyclic Enediyne

A short and efficient synthesis of cinnoline-fused cyclic enediyne is reported. Richter cyclization of o-(1,3-butadiynyl)phenyltriazene produced 3-alkynyl-4-bromocinnoline. The Sonogashira coupling of the latter with 5-hexyn-1-ol was employed for the introduction of a second acetylenic moiety. The c...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-08, Vol.76 (16), p.6937-6941
Main Authors: Vinogradova, Olga V, Balova, Irina A, Popik, Vladimir V
Format: Article
Language:English
Subjects:
Cyclization
Enediynes - chemical synthesis
Enediynes - chemistry
Heterocyclic Compounds, 2-Ring - chemistry
Molecular Structure
Temperature
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Summary:A short and efficient synthesis of cinnoline-fused cyclic enediyne is reported. Richter cyclization of o-(1,3-butadiynyl)phenyltriazene produced 3-alkynyl-4-bromocinnoline. The Sonogashira coupling of the latter with 5-hexyn-1-ol was employed for the introduction of a second acetylenic moiety. The crucial cyclization step was achieved under Nozaki–Hiyama–Kishi conditions. Cinnoline-fused 10-membered ring enediyne is more reactive than corresponding carbocyclic analog and produces good yield of the Bergman cyclization product upon mild heating. This enediyne induces single-strand dDNA scissions upon incubation at 40 °C.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo201148h