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Synthesis of 2,6‐bis(1 H ‐indole‐6‐yl)‐4 H ‐pyran‐4‐ones via Leimgruber–Batcho indole synthesis
Author(s) -
Shahrisa Aziz,
Ghasemi Zarrin,
Saraei Mahnaz
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.80
Subject(s) - chemistry , enamine , pyran , indole test , octane , bicyclic molecule , medicinal chemistry , stereochemistry , organic chemistry , catalysis
2,6‐Bis(1 H ‐indole‐6‐yl)‐4 H ‐pyran‐4‐one 4 was synthesized via Leimgruber–Batcho methodology starting from 2,6‐bis(4‐methyl‐3‐nitrophenyl)‐4 H ‐pyran‐4‐one 2 . Enamine intermediate in this reaction, 3 , reacts with aroyl chlorides in the presence of 1,4‐diazabicyclo[2.2.2]octane in dioxane to give the substituted enamines 8a , 8b , 8c . Enamines 8a , 8b undergo reductive cyclization with Fe/AcOH to the corresponding 3‐aroylindoles 10a ,10b . J. Heterocyclic Chem., 46 , 273 (2009).