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- Publisher
- Wiley
- Copyright
- © 2021 Wiley‐VCH GmbH
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.202100401
- Publisher site
- See Article on Publisher Site
Abstract
The DABCO promoted domino reaction of 1‐(2‐hydroxyphenyl)‐3‐phenylprop‐2‐en‐1‐ones and alkyl propiolate or dialkyl but‐2‐ynedioate in toluene at high temperature resulted in methyl 3‐(2‐hydroxybenzoyl)‐1‐naphthoates or dimethyl 3‐(2‐hydroxybenzoyl)naphthalene‐1,2‐dicarboxylate in moderate to good yields. The hydroxyl group played a crucial rule in the reaction. The reaction mechanism of this formal [4+2] cycloaddition reaction was believed with initially formation of methyl 3‐(2‐cinnamoylphenoxy)acrylate, intramolecular Diels‐Alder reaction, ring‐opening of benzo[b]xanthene and aromatization process.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Oct 1, 2021
Keywords: [4+2]cycloaddition; Diels-Alder reaction; chalcone; electron-deficient alkyne; naphthalene; annulation reaction