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Synthesis of 2,5-diaminopyrazine derivatives via dimerization of 2H-azirin-3-amines


Mekhael, M K G; Linden, A; Heimgartner, H (2008). Synthesis of 2,5-diaminopyrazine derivatives via dimerization of 2H-azirin-3-amines. Heterocycles, 76(1):689-698.

Abstract

The 2-monosubstituted 2H-azirin-3-amine (5c) was prepared conveniently by subsequent treatment of N-methyl-N-phenylpropanamide in THF with LDA, diphenyl phosphorochloridate (DPPCl), and sodium azide in DMF. In the absence of nucleophiles, the reaction of 5c in THF with BF3·OEt2 at -78°C yields 2,5-dihydro-2,5-dimethyl-3,6-bis(N-methyl-N-phenylamino)pyrazinium tetrafluoroborate (11). Treatment of the latter with NaOH yields the corresponding 2,5-dihydropyrazine derivative (12), whereas dehydrogenation with DDQ leads to 2,5-dimethyl-3,6-bis(N-methyl-N-phenylamino)pyrazine (13). The structures of 12 and 13 were established by X-ray crystallography.

Abstract

The 2-monosubstituted 2H-azirin-3-amine (5c) was prepared conveniently by subsequent treatment of N-methyl-N-phenylpropanamide in THF with LDA, diphenyl phosphorochloridate (DPPCl), and sodium azide in DMF. In the absence of nucleophiles, the reaction of 5c in THF with BF3·OEt2 at -78°C yields 2,5-dihydro-2,5-dimethyl-3,6-bis(N-methyl-N-phenylamino)pyrazinium tetrafluoroborate (11). Treatment of the latter with NaOH yields the corresponding 2,5-dihydropyrazine derivative (12), whereas dehydrogenation with DDQ leads to 2,5-dimethyl-3,6-bis(N-methyl-N-phenylamino)pyrazine (13). The structures of 12 and 13 were 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:May 2008
Deposited On:06 Feb 2009 12:46
Last Modified:18 Apr 2018 11:39
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation (SNF), F. Hoffmann-La Roche AG, Basel
OA Status:Closed
Official URL:http://www.heterocycles.jp/library/journalResult.php?-skip=30
Related URLs:http://www.heterocycles.jp/index.php (Publisher)
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation (SNF)
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel

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