α-(benzotriazol-1-yl)propargyl ethyl ethers: Novel precursors to enediynes, enynes and dienynes

Article abstract of DOI:10.1080/00397919608003826

Deprotonated 1-(benzotriazol-1-yl)propargyl ethyl ethers react with propargyl, allyl and alkyl bromides to give the expected substituted derivatives 2, 4 and 9, respectively. Subsequent eliminations of the benzotriazolyl group upon treatment with NaH or ZnBr₂, and elaboration of the acetylene group, generate ethoxy substituted enediynes 3, 6, 8, dienynes 7 and enynes 12. Grignard reagents or LiAlH₄ convert 9 into 2a-ethoxy substituted alkynes 10 and 11.

Full text of DOI:10.1080/00397919608003826

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Synthetic Communications: An
International Journal for Rapid
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Organic Chemistry
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α-(Benzotriazol-1-YL)Propargyl
Ethyl Ethers: Novel Precursors
to Enediynes, Enynes and
Dienynes
Alan R. Katritzky a , Zhongxing Zhang a & Hengyuan
Lang a
a Center for Heterocyclic Compounds, Department
of Chemistry , University of Florida , Gainesville,
Florida, 32611–7200
Published online: 23 Aug 2006.
To cite this article: Alan R. Katritzky , Zhongxing Zhang & Hengyuan Lang (1996)
α-(Benzotriazol-1-YL)Propargyl Ethyl Ethers: Novel Precursors to Enediynes,
Enynes and Dienynes, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 26:21, 4049-4064, DOI:
10.1080/00397919608003826
To link to this article: http://dx.doi.org/10.1080/00397919608003826
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