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Synthesis of perhydropyrrolo[1,2-a]pyrazine-1,4-diones and their sulfur-analogues by ring-enlargement of N-(2H-azirin-3-yl)-L-prolinates


Budzowski, Artur; Linden, Anthony; Heimgartner, Heinz (2004). Synthesis of perhydropyrrolo[1,2-a]pyrazine-1,4-diones and their sulfur-analogues by ring-enlargement of N-(2H-azirin-3-yl)-L-prolinates. Heterocycles, 64(1):417-435.

Abstract

The hydrolysis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate (1c) at 50°C in the presence of silica gel afforded (S)-perhydro-3,3-dimethylpyrrolo[1,2-a]pyrazine-1,4-dione ((S)-4a), which was thionated chemoselectively to give the corresponding 1-thioxo derivative ((RS)-5a) as a racemic mixture. On the other hand, treatment of 1c with hydrogen sulfide led to the 4-thioxo isomer ((S)-6a). Thionation with Lawesson reagent yielded the bisthioxo compound ((RS)-7a), again as a racemate. Analogous reactions were carried out with the heterospirocyclic N-(2H-azirin-3-yl)-L-prolinates (1d) and (1e). The structures of (RS)-5a, (S)-6a-c, and (RS)-7a have been established by X-Ray crystallography.

Abstract

The hydrolysis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate (1c) at 50°C in the presence of silica gel afforded (S)-perhydro-3,3-dimethylpyrrolo[1,2-a]pyrazine-1,4-dione ((S)-4a), which was thionated chemoselectively to give the corresponding 1-thioxo derivative ((RS)-5a) as a racemic mixture. On the other hand, treatment of 1c with hydrogen sulfide led to the 4-thioxo isomer ((S)-6a). Thionation with Lawesson reagent yielded the bisthioxo compound ((RS)-7a), again as a racemate. Analogous reactions were carried out with the heterospirocyclic N-(2H-azirin-3-yl)-L-prolinates (1d) and (1e). The structures of (RS)-5a, (S)-6a-c, and (RS)-7a have been 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:2004
Deposited On:25 Apr 2013 09:33
Last Modified:07 Dec 2017 20:59
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Dr. Helmut Legerlotz-Stiftung, University of Zurich, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.3987/COM-04-S(P)43

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