Intramolecular Diels-Alder reactions of 6-azalumazines and 6-azapterins. A facile route to 6,7-annulated 5-deazapteridines
✍ Scribed by Taylor, Edward C.; Warner, John C.; Pont, Joseph L.
- Book ID
- 120991909
- Publisher
- American Chemical Society
- Year
- 1988
- Tongue
- English
- Weight
- 551 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0022-3263
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A concise synthesis of the macrocyclic vinylbutenolide 19 is described, based on a facile RCM reaction of the substrates 16/18. Treatment of 19 with TFA containing water led to the 5,6,7-tricyclic compound 27, in a single step, in >90% yield, rather than to the alternative ring system 23 found in pl
## Abstract N‐Acyl‐N‐(4‐penten‐1‐yl)‐1‐amino‐1, 3‐butadiene (1) isomerisieren sich bei 190–215° über eine intramolekulare __Diels__‐__Alder__‐Reaktion stereoselektiv zu cis‐ verknüpften Octahydro‐chinolinen 2. Unter den gleichen Bedingungen erhält man aus dem N(Pent‐4‐enoyl)‐N‐propyl‐1‐amino−1, 3‐b