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Synthesis of 2,6-bis(1H-indole-6-yl)-4H-pyran-4-ones via Leimgruber–Batcho indole synthesis

✍ Scribed by Aziz Shahrisa; Zarrin Ghasemi; Mahnaz Saraei

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
113 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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).

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