Condensation of Ethyl Acetoacetate with Naphthalene-Diols. The Synthesis of some Novel Coumarins and Chromones. Part 1

✍ Scribed by Ulku Oyman; Keriman Gunaydin

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 189 KB
• Volume: 103
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19941031208

✦ Synopsis

Abstract

In Simonis reaction with ethyl acetoacetate naphthalene‐2,6‐diol gives 8‐hydroxy‐3‐methyl‐1H‐naphtho[2,1‐b]‐pyran‐1‐one and naphthalene‐2,7‐diol gives the related 9‐hydroxy isomer. In Pechman reactions, the former diol yields a coumarin, 8‐hydroxy‐1‐methyl‐3H‐naphtho[2,1‐b]‐pyran‐3‐one, with the corresponding orientation, but the latter diol gives a coumarin, 8‐hydroxy‐4‐methyl‐2H‐naphtho[2,3‐b]‐pyran‐2‐one, with an unusual linear annelation pattern.