Intramolecular cyclization of a dieno-nitrile: synthesis of a new monoterpene alkaloid
β Scribed by Yasuo Butsugan; Shigeo Yoshida; Masao Muto; Tadaaki Bito; Teruo Matsuura; Ruka Nakashima
- Publisher
- Elsevier Science
- Year
- 1971
- Tongue
- French
- Weight
- 94 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
We wish to report an intramolecular cyclisation between nitrile and conjugated diene moieties leading to a monoterpene alkaloid with a pyridine nucleus. Rose bengal-sesitized photooxygenation of (-)-citronellonitrile' (&) in methanol followed by reduction of the
π SIMILAR VOLUMES
The dehydration of amides or aldoximes to yield nltriles generally requires Lewis acids and vigorous reaction conditions, which prevent one from applying the method to thermally labile nitriles. Recently sane efforts have been made to achieve the dehydratlon under milder conditions. For example, am
## Abstract Nitriles can be obtained in good yields (60β80%) by treatment with oxygen at 30Β° of a methanolic solution of the corresponding aldehyde, containing ammonia, a strong base and a catalytically active copper complex. Yields are lower for baseβsensitive aldehydes. In a similar way, but in