Publication: Umsetzungen von 3-(Dimethylamino)-2,2-dimethyl-2H-azirim mit Barbitursäure-Derivaten
Umsetzungen von 3-(Dimethylamino)-2,2-dimethyl-2H-azirim mit Barbitursäure-Derivaten
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Schläpfer-Dähler, M., & Heimgartner, H. (1990). Umsetzungen von 3-(Dimethylamino)-2,2-dimethyl-2H-azirim mit Barbitursäure-Derivaten. Helvetica Chimica Acta, 73, 2275–2286. https://doi.org/10.1002/hlca.19900730824
Abstract
Abstract
Abstract
The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) and 5,5-disubstituted barbituric acids 5 in i-PrOH at ca. 70° gives 2-[5-(dimethylamino)-4,4-dimethyl-4H-imidazol-2-y1]alkanamides of type 6 in good yields (Scheme 1). The formation of 6 proceeds with loss of CO2; various reaction mechanisms with a zwitterionic 1:1 adduct B as common intermediate are discussed (Schemes 2 and 5). Thermolysis of product 6 leads to 2-alkyl-5-(dimethylamino)-4,4-dimethyl-4H-imidazoles 8 or the tautomeric 2-alkylidene derivatives 8' via eliminat
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- Schläpfer-Dähler, Marlise
- Heimgartner, Heinz
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Citations
Schläpfer-Dähler, M., & Heimgartner, H. (1990). Umsetzungen von 3-(Dimethylamino)-2,2-dimethyl-2H-azirim mit Barbitursäure-Derivaten. Helvetica Chimica Acta, 73, 2275–2286. https://doi.org/10.1002/hlca.19900730824
