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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


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.

Abstract

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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:March 2011
Deposited On:09 Mar 2011 13:31
Last Modified:05 Apr 2016 14:52
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:F. Hoffmann-La Roche AG, Basel
Publisher DOI:10.3987/COM-10-S(E)73
Permanent URL: http://doi.org/10.5167/uzh-47460

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