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A new approach to morpholin-2-one derivatives via the reaction of β-amino alcohols with dicyanofumarates


Mlostoń, Grzegorz; Pieczonka, Adam M; Korany, A Ali; Linden, Anthony; Heimgartner, Heinz (2012). A new approach to morpholin-2-one derivatives via the reaction of β-amino alcohols with dicyanofumarates. ARKIVOC, 2012(iii):181-192.

Abstract

A novel approach for the synthesis of morpholin-2-one derivatives from dialkyl dicyanofumarates and β-amino alcohols is presented. The reaction takes place under mild conditions via an addition-elimination-lactonization pathway. The formation of the six- membered ring occurs selectively leading to a single diastereomer. In contrast to arylhydrazines, the reaction of hydrazine hydrate with dicyanofumarates yields pyrazol-3(2H)-ones and not 5-aminopyrazoles.

Abstract

A novel approach for the synthesis of morpholin-2-one derivatives from dialkyl dicyanofumarates and β-amino alcohols is presented. The reaction takes place under mild conditions via an addition-elimination-lactonization pathway. The formation of the six- membered ring occurs selectively leading to a single diastereomer. In contrast to arylhydrazines, the reaction of hydrazine hydrate with dicyanofumarates yields pyrazol-3(2H)-ones and not 5-aminopyrazoles.

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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
Scopus Subject Areas:Physical Sciences > Organic Chemistry
Language:English
Date:23 January 2012
Deposited On:02 Apr 2012 07:20
Last Modified:30 Jul 2020 03:27
Publisher:Arkat USA Inc
ISSN:1551-7004
Funders:European Social Fund ‘HUMAN – BEST INVESTMENT!’
OA Status:Gold
Publisher DOI:https://doi.org/10.3998/ark.5550190.0013.314
Official URL:http://www.arkat-usa.org/get-file/42701

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