title: Reactions of 1,2-diaza-1,3-butadienes with propargyl alcohol as an approach to novel bi-heterocyclic systems.
abstract: Here we describe the reaction of 1,2-diaza-1,3-dienes and propargyl alcohol furnishing α-(prop-2-yn-1-yloxy)hydrazones that are converted into novel alkyl-1-oxa-7,8-diazaspiro[4.4]nona-3,8-dien-6-ones, by means of 2,3-Wittig rearrangement under very mild conditions. The same α-(prop-2-yn-1-yloxy)hydrazones, treated with benzyl azides furnish the corresponding α-[(1,2,3-triazol-4-yl)methoxy]hydrazones, via Cu(ii)-catalyzed 1,3-dipolar cycloaddition. Their subsequent base-promoted cyclization produces interesting pyrazolone-triazole derivatives. The impact of this work can be ascribable to the attractiveness of the bi-heterocyclic systems obtained and to the ease of the synthetic methodologies proposed.
authors.affiliation: Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, PU, Italy. fabio.mantellini@uniurb.it lucia.decrescentini@uniurb.it.
authors.forename: L
authors.initials: L
authors.lastname: De Crescentini
authors.affiliation: Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, PU, Italy. fabio.mantellini@uniurb.it lucia.decrescentini@uniurb.it.
authors.forename: F R
authors.initials: FR
authors.lastname: Perrulli
authors.affiliation: Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, PU, Italy. fabio.mantellini@uniurb.it lucia.decrescentini@uniurb.it.
authors.forename: G
authors.initials: G
authors.lastname: Favi
authors.affiliation: Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, PU, Italy. fabio.mantellini@uniurb.it lucia.decrescentini@uniurb.it.
authors.forename: S
authors.initials: S
authors.lastname: Santeusanio
authors.affiliation: Department of Chemistry, University of Siena, Via Aldo Moro, 53100 Siena, Italy.
authors.forename: G
authors.initials: G
authors.lastname: Giorgi
authors.affiliation: Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, PU, Italy. fabio.mantellini@uniurb.it lucia.decrescentini@uniurb.it.
authors.forename: O A
authors.initials: OA
authors.lastname: Attanasi
authors.affiliation: Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, PU, Italy. fabio.mantellini@uniurb.it lucia.decrescentini@uniurb.it.
authors.forename: F
authors.initials: F
authors.lastname: Mantellini