ArticleMolecules (Basel, Switzerland)2026
A Molecular Electron Density Theory Study of the Domino [4+2]/[3+2] Cycloaddition Leading to a Tricyclic 1,2-Oxazine Nitrones.
Article in Molecules (Basel, Switzerland), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The reaction of 2,5-dimethylfuran (DMF) with two equivalents of α-nitrosostyrene (NS) leading to a tricyclic 1,2-oxazine nitrone (TON) has been examined theoretically at the ωB97X-D/6-311G(d,p) computational level. In this case, the domino process should be considered: (i) a [4+2] cycloaddition (42CA) between DMF and NS yielding a bicyclic 1,2-oxazine (BO); and (ii) a second formal [3+2] cycloaddition (32CA) reaction between BO and NS yielding the final TON. Analysis of the reactivity indices shows that DMF and BO generated along the first 42CA reaction are strong nucleophiles, while NS is a strong electrophile. The first 42CA reaction takes place according to a one-step mechanism. In turn, the second 32CA proceeds according to a two-step mechanism through the zwitterionic intermediate
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