Domino Reactions - One-pot Preparation of Fluoreno[2,3,4-ij]isoquinoline Derivatives From Conjugated Ketene Imines
(1991) The Journal of Organic Chemistry — Vol. 56, n° 12, p. 4008-4016 (1991)
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- Abstract
- Iminophosphoranes 4, derived from ethyl alpha-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160-degrees-C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/second ring closure/double aromatization process to give isoquinoline derivatives 7 and/or the previously unknown fluoreno[2,3,4-ij]isoquinolines 9 in moderate yields. Similarly, iminophosphoranes 14 derived from ethyl alpha-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160-degrees-C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.
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Citations
Molina, P., Alajarin, M., Vidal, A., Fenaudupont, J., & Declerq, JP. (1991). Domino Reactions - One-pot Preparation of Fluoreno[2,3,4-ij]isoquinoline Derivatives From Conjugated Ketene Imines. The Journal of Organic Chemistry, 56(12), 4008-4016. https://doi.org/10.1021/jo00012a039 (Original work published 1991)