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Synthesis of Pyrano[3,2‐ b ]indole Derivatives Based on Intramolecular Hetero‐ DielsAlder of 2‐Benzylidene‐2,3‐dihydro‐1 H ‐indol‐3‐ones
Author(s) -
Davion Yann,
Joseph Benoît,
Bénéteau Valérie,
Léger JeanMichel,
Jarry Christian,
Mérour JeanYves
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390218
Subject(s) - chemistry , intramolecular force , indole test , diels–alder reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Pyrano[3,2‐ b ]indole derivatives 2 – 6 were synthesized in good yields from 1‐acetyl‐2‐benzylidene‐2,3‐dihydro‐1 H ‐indol‐3‐ones 8 and 13 – 15 by an intramolecular hetero‐ DielsAlder reaction. The structures of compounds 2a, 3a, 4, 5 , and 6 were unambiguously established by X‐ray analysis. Compounds 4 and 5 were further aromatized to the corresponding derivatives 16 and 17 , respectively.