A new synthesis of substituted 4-dialkylaminopyridines was developed, starting from 3-nitropyran-2-one N-functionalized amidines. Secondary amines were reacted with the amidines in a sealed tube and in ethanol as the solvent yielding exclusively 4-dialkylaminopyridine derivatives or a mixture with 4-methylpyridine derivative, depending on the C-a-linked substituents of the starting amidine. Structural elucidation of the 4-dialkylaminopyridines revealed their existence as two tautomeric forms, depending on the solvent
Synthesis of 4-dialkylaminopyridine derivatives through ring-rearrangement of 3-nitro-2H-pyran-2-one acetamidines / V. Bertacche, A. Contini, E. Erba, D. Nava, P. Trimarco. - In: TETRAHEDRON. - ISSN 0040-4020. - 63:39(2007), pp. 9652-9662.
Titolo: | Synthesis of 4-dialkylaminopyridine derivatives through ring-rearrangement of 3-nitro-2H-pyran-2-one acetamidines |
Autori: | BERTACCHE, VITTORIO (Primo) CONTINI, ALESSANDRO (Secondo) NAVA, DONATELLA (Penultimo) TRIMARCO, PASQUALINA (Ultimo) |
Parole Chiave: | 3-Nitro-2H-pyran-2-one amidines ; 4-Dialkylamino-a-nitromethylpyridines ; Tautomerism ; Thermal rearrangement |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 2007 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tet.2007.07.022 |
Appare nelle tipologie: | 01 - Articolo su periodico |