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Synthesis and Reactions of 1-(3-Chloropropyl)-6,7-dimethoxy-3-methylbenzo[c]pyrylium Perchlorate

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Acid-catalyzed acylation of 3,4-dimethoxyphenylacetone with γ-chlorobutyryl chloride gave 1-(3-chloropropyl)-6,7-dimethoxy-3-methylbenzo[c]pyrylium perchlorate. Recyclization of the product with nitrogen nucleophiles (ammonia, primary amines, hydrazine derivatives, hydroxylamine) led through the corresponding isoquinolinium salts to benzo[f]indolizinium, pyridazino[2,1-b]isoquinolinium, and 1,2-oxazino[2,1-b]isoquinolinium salts.

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Authors and Affiliations

  1. L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk, Ukraine

    A. V. Kibalny, A. A. Afonin & V. I. Dulenko

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  1. A. V. Kibalny
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  2. A. A. Afonin
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  3. V. I. Dulenko
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Kibalny, A.V., Afonin, A.A. & Dulenko, V.I. Synthesis and Reactions of 1-(3-Chloropropyl)-6,7-dimethoxy-3-methylbenzo[c]pyrylium Perchlorate. Chemistry of Heterocyclic Compounds 40, 1131–1136 (2004). https://doi.org/10.1023/B:COHC.0000048284.17694.d0

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