Abstract
Reaction of salicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in diethylaniline under reflux gave coumarins (3) in moderate to high yield except 3-methoxycarbonylsalicylaldehyde (1e). 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 |
| Publication status | Published - 1994 |
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Keywords
- bromocoumarin
- coumarin synthesis
- methoxycarbonylcoumarin
- salicylaldehyde
- substituent effect
- Wittig reaction
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
- Drug Discovery
- Pharmacology
Cite this
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.