(Chemical Equation Presented) With the goal of their exploitation for the synthesis of heterocycles, sulfides 10 and sulfones 11, derived from the initial ring-opening of 2-nitrothiophene (5) with pyrrolidine/AgNO3 in EtOH, were reacted with diazomethane. Interesting dichotomic behavior was found to yield pyrazolines 17 from 10 and isoxazolines 18 (as the main products) from 11. Intriguingly enough, in the latter case, an unexpected apparent C-C methylene insertion was also observed, leading to the homologous cyclopropanes 19 as secondary products. © 2007 American Chemical Society.
Bianchi, L., Giorgi, G., Maccagno, M., Petrillo, G., Rocca, V., Sancassan, F., et al. (2007). Butadienic Building Blocks from 2-Nitrothiophene as Precursors of Nitrogen Heterocycles: Intriguing Dichotomic Behavior. JOURNAL OF ORGANIC CHEMISTRY, 72(24), 9067-9073 [10.1021/jo701460k].
Butadienic Building Blocks from 2-Nitrothiophene as Precursors of Nitrogen Heterocycles: Intriguing Dichotomic Behavior
Giorgi G.;
2007-01-01
Abstract
(Chemical Equation Presented) With the goal of their exploitation for the synthesis of heterocycles, sulfides 10 and sulfones 11, derived from the initial ring-opening of 2-nitrothiophene (5) with pyrrolidine/AgNO3 in EtOH, were reacted with diazomethane. Interesting dichotomic behavior was found to yield pyrazolines 17 from 10 and isoxazolines 18 (as the main products) from 11. Intriguingly enough, in the latter case, an unexpected apparent C-C methylene insertion was also observed, leading to the homologous cyclopropanes 19 as secondary products. © 2007 American Chemical Society.
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https://hdl.handle.net/11365/9903
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