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Reaktion von 3-Dimethylamino-2,2-dimethyl-2H-azirin mit Barbitursäure


Link, Helmut; Bernauer, Karl; Daly, John J; Chaloupka, Stanislav; Heimgartner, Heinz (1981). Reaktion von 3-Dimethylamino-2,2-dimethyl-2H-azirin mit Barbitursäure. Helvetica Chimica Acta, 64(1):49-63.

Abstract

Reaction of 3-Dimethylamino-2,2-dimethyl-2H-azirine with Barbituric Acid.
The reaction of 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with barbituric acid (4) in dimethyl formamide at room temperature yields a mixture of several compounds. The two main products 5 and 6 have been isolated in 40 and 10% yield, respectively, and their structures established by X-ray analysis. In Schemes 4-6 reaction mechanisms for the formation of 5 and 6 are postulated, the first step beeing either a C- or an N-alkylation of barbituric acid.
Reduction of 5 and 6 with NaBH4 in ethanol at room temperature yields 6,6-dimethyl-1,5,6,7-tetrahydro-pyrrolo[2,3-d]pyrimidin-2,4(3H)-dione (7) and 3,3-dimethy1-2,3-dihydro-imidazo[1,2-c]pyrimidin-5,7(1H,6H)-dione (8) in 38 and 48% yield, respectively. Treatment of 6 with 3N aqueous NaOH at room temperature gives 3,3-dimethyl-imidazo[1,2-c]pyrimidin-2,5,7(1H,3H,6H)-trione (9) in 51% yield (Scheme 3).

Abstract

Reaction of 3-Dimethylamino-2,2-dimethyl-2H-azirine with Barbituric Acid.
The reaction of 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with barbituric acid (4) in dimethyl formamide at room temperature yields a mixture of several compounds. The two main products 5 and 6 have been isolated in 40 and 10% yield, respectively, and their structures established by X-ray analysis. In Schemes 4-6 reaction mechanisms for the formation of 5 and 6 are postulated, the first step beeing either a C- or an N-alkylation of barbituric acid.
Reduction of 5 and 6 with NaBH4 in ethanol at room temperature yields 6,6-dimethyl-1,5,6,7-tetrahydro-pyrrolo[2,3-d]pyrimidin-2,4(3H)-dione (7) and 3,3-dimethy1-2,3-dihydro-imidazo[1,2-c]pyrimidin-5,7(1H,6H)-dione (8) in 38 and 48% yield, respectively. Treatment of 6 with 3N aqueous NaOH at room temperature gives 3,3-dimethyl-imidazo[1,2-c]pyrimidin-2,5,7(1H,3H,6H)-trione (9) in 51% yield (Scheme 3).

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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 > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry
Language:German
Date:1981
Deposited On:24 Jul 2014 07:26
Last Modified:30 Jul 2020 14:03
Publisher:Wiley-Blackwell
ISSN:0018-019X
OA Status:Green
Publisher DOI:https://doi.org/10.1002/hlca.19810640108

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