Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-47460
Löpfe, M; Heimgartner, H; Linden, A (2011). N-Methyl-N-phenyl-5-oxa-1-azaspiro[2.5]oct-1-en-2-amine — Synthesis and Reactions of a Synthon for an Unknown α-Amino Acid. Heterocycles, 82(2):1267-1282.
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The synthesis of the heterospirocyclic amino azirine N-methyl-N-phenyl-5-oxa-1-azaspiro[2.5]oct-1-en-2-amine (6a) was achieved from 3,4-dihydro-2H-pyrane (7) via N-methyl-N-phenyltetrahydropyran- 3-thiocarboxamide (11). The reactions of 6a with thiobenzoic acid and Z-Phe-OH, respectively, leading to the corresponding 3-benzoylaminotetrahydropyran- 3-thiocarboxamide (13) and the diastereoisomeric dipeptide amides (14), respectively, demonstrate that 6a is a valuable synthon for the hitherto unknown 3-aminotetrahydropyrane-3-carboxylic acid. The structure of 13 was established by X-Ray crystallography.
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|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Department of Chemistry|
|Deposited On:||09 Mar 2011 13:31|
|Last Modified:||10 Jul 2014 21:49|
|Publisher:||The Japan Institute of Heterocyclic Chemistry|
|Funders:||F. Hoffmann-La Roche AG, Basel|
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