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Cyclization vs. Elimination Reactions of 5-Aryl-5-hydroxy 1,3-Diones: One-Pot Synthesis of 2-Aryl-2,3-dihydro-4H-pyran-4-ones

✍ Scribed by Rasheed Ahmad Khera; Rasheed Ahmad; Ihsan Ullah; Obaid-Ur-Rahman Abid; Olumide Fatunsin; Muhammad Sher; Alexander Villinger; Peter Langer

Publisher: John Wiley and Sons
Year: 2010
Tongue: German
Weight: 222 KB
Volume: 93
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.201000015

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✦ Synopsis

Abstract

2‐Aryl‐2,3‐dihydro‐4__H__‐pyran‐4‐ones were prepared in one step by cyclocondensation of 1,3‐diketone dianions with aldehydes. The use of HCl (10%) for the aqueous workup proved to be very important to avoid elimination reactions of the 5‐aryl‐5‐hydroxy 1,3‐diones formed as intermediates. The TiCl~4~‐mediated cyclization of a 2‐aryl‐2,3‐dihydro‐4__H__‐pyran‐4‐one with 1,3‐silyloxybuta‐1,3‐diene resulted in cleavage of the pyranone moiety and formation of a highly functionalized benzene derivative.

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