The peptido-mimetic reaction between 4-dialkylaminocarbonyl-1,2-diaza-1,3-butadienes and sarcosine ethyl ester gave alfa-aminohydrazones. In ethanol under reflux with sodium hydride, these compounds furnished new and unexpected 7-oxo-8-oxa-2,3,6-triazabicyclo[3.2.1]oct-3-ene-2-carboxylates and 5-oxo-4,5-dihydro-2-pyrazines. By treatment with Amberlyst 15H in acetone:water (10:1), the same hydrazones were converted into the corresponding ethyl 2-[{1-[(diethylamino)carbonyl]-2-oxopropyl}(methyl)amino]acetates.
Unusual Peptido-mimetic Reaction of 1,2-Diaza-1,3-butadienes: Straightforward Entry to 2,3,6-Triazabicyclo[3.2.1]oct-3-enes, 5-Oxo-4,5-dihydro-2-pyrazines and 2-Carbonyl-2-oxopropylaminoacetates / O. A. Attanasi; L. De Crescentini; P. Filippone; G. Giorgi; F. Mantellini; A. Mazzanti. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 15:(2006), pp. 2403-2406. [10.1055/s-2006-950409]
Unusual Peptido-mimetic Reaction of 1,2-Diaza-1,3-butadienes: Straightforward Entry to 2,3,6-Triazabicyclo[3.2.1]oct-3-enes, 5-Oxo-4,5-dihydro-2-pyrazines and 2-Carbonyl-2-oxopropylaminoacetates.
MAZZANTI, ANDREA
2006
Abstract
The peptido-mimetic reaction between 4-dialkylaminocarbonyl-1,2-diaza-1,3-butadienes and sarcosine ethyl ester gave alfa-aminohydrazones. In ethanol under reflux with sodium hydride, these compounds furnished new and unexpected 7-oxo-8-oxa-2,3,6-triazabicyclo[3.2.1]oct-3-ene-2-carboxylates and 5-oxo-4,5-dihydro-2-pyrazines. By treatment with Amberlyst 15H in acetone:water (10:1), the same hydrazones were converted into the corresponding ethyl 2-[{1-[(diethylamino)carbonyl]-2-oxopropyl}(methyl)amino]acetates.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
