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Diels-alder reactions of pyrano[3,4-b]indol-3-ones with substituted alkenes : synthesis of 1,2-dihydrocarbazoles - part II

✍ Scribed by P. Van Doren; F. Compernolle; G. Hoornaert

Book ID
108372473
Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
437 KB
Volume
46
Category
Article
ISSN
0040-4020

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Diels-alder reactions of pyrano[3,4-b]in
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The role of the substitution pattern on the stability of the obtained 1.2-dihydreearbazolee is interpreted In terms of electronic and steric effects on the aromatization to the corresponding carbazoles. CH and 2-CHb bonds, a small coupling constant of 1,6 Hz is observed. A dihedral angle of about 26

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## Abstract 3‐Indolylalkanoic acids 2 react with benzoic acid anhydride under catalysis of Et~2~O ‐ ZnCl~2~ and mild conditions to furnish the 1‐phenyl‐substituted pyrano[3,4‐__b__]indol‐3‐ones 1c, 1d, and 3a, 3b. Products 1c, 1d, and 3b may be converted into the novel functionalized carbazoles 4 a