A Novel Rearrangement of Cyclic Glutamine Derivatives: Ring Contraction in 3,6-Diamino-2,3,4,5-tetrahydropyridin-2-ones to Yield 5-Iminoproline Amides
2011 | journal article. A publication with affiliation to the University of Göttingen.
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A Novel Rearrangement of Cyclic Glutamine Derivatives: Ring Contraction in 3,6-Diamino-2,3,4,5-tetrahydropyridin-2-ones to Yield 5-Iminoproline Amides
Belov, V. N.; Sokolov, V. V.; Zlatopolskiy, B. D. & de Meijere, A. (2011)
European Journal of Organic Chemistry,(22) pp. 4093-4097. DOI: https://doi.org/10.1002/ejoc.201100404
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- Authors
- Belov, Vladimir N.; Sokolov, Viktor V.; Zlatopolskiy, Boris D.; de Meijere, Armin
- Abstract
- A new rearrangement of the cyclic L-glutamine derivative (S)-6-carbamoylamino-3-(methylamino)-2,3,4,5-tetrahydropyridin-2-one (2) and its descarbamoyl analogue 10-H was found to yield enantiomerically pure 5-carbamoylimino-1-methyl-L-proline amide (12-CONH(2)) and its descarbamoyl analogue 12-H, respectively. Cyclic amidines 2 and 10-H were generated from the amide N(2)-ZGlnOEt 3 in seven and six steps, respectively. Deprotection of (S)-6-amino-3-[(N-benzyloxycarbonyl-N-methyl)amino]-2,3,4,5-tetrahydropyridin-2-one (8) led directly to 5-iminoproline amide 12-H (via 10-H and the bicyclic orthoamidine 11-H) in 66% overall yield from 3. Carbamoylation of 8 with ZNCO (Z = PhCH(2)OCO) followed by hydrolytic removal of both Z groups gave 5-(carbamoylimino)proline amide 12-CONH(2) (via 2 and orthoamidine 11-CONH(2)) in 70% overall yield from 3.
- Issue Date
- 2011
- Status
- published
- Publisher
- Wiley-blackwell
- Journal
- European Journal of Organic Chemistry
- ISSN
- 1434-193X
- Sponsor
- Bayer AG