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Smith, M. B., Science of Synthesis, (2005) 21, 704.
The direct oxidation of nitrogen heteroaromatic compounds is a potentially attractive route to unsaturated lactams. In practice, this approach is limited, but useful for specific compounds. The oxidation of pyrrole is well known, and a limited number of oxidants are available.[243,244] Pyrrole and alkylpyrroles also undergo autoxidation, but this reaction has not been well studied.[245,246] Although oxidation is not a general route to lactams, simple unsaturated pyrrolidin-2-ones can be quickly accessed. For example, the direct oxidation of a dilute solution of pyrrole with aqueous hydrogen peroxide, gives 1,5-dihydropyrrolidin-2-one (180) and 1,3-dihydropyrrolidin-2-one (181) in a ratio of 9:1 in about 30% yield (Scheme 84).[247]
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References
[243] | Meeeee, M.; Meeee, M., Meee. Meee. Meee., (8888) 88, 888. |
[244] | Meeeeee, M.; Meeee, M., Meee. Meee. Meee., (8888) 88, 888. |
[245] | Möee, M.; Meeeeeeee, M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
[246] | Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[247] | Meeeee, M.; Meeeeeee, M.; Meeeeee, M. M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 888.