Abstract
Reaction of salicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in diethylaniline under reflux gave coumarins (3) in moderate to high yield except 3-methoxycarbonylsalicylaldehyde (le) as summarized in Table I. The substituent effects are discussed. A substituent at C6 on 1 usually facilitated the formation of the coumarin ring regardless of its electronic character.
| Original language | English |
|---|---|
| Pages (from-to) | 2170-2173 |
| Number of pages | 4 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 42 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - Jan 1 1994 |
Keywords
- Keywords salicylaldehyde
- Wittig reaction
- bromocoumarin
- coumarin synthesis
- methoxycarbonyl-coumarin
- substituent effect
ASJC Scopus subject areas
- Chemistry(all)
- Drug Discovery
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Harayama, T., Nakatsuka, K., Nishioka, H., Murakami, K., Hayashida, N., & Ishii, H. (1994). Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II: Synthesis of Bromo- and Methoxycarbonylcoumarins. Chemical and Pharmaceutical Bulletin, 42(10), 2170-2173. https://doi.org/10.1248/cpb.42.2170