A new and efficient synthesis of 4-functionalized benzo[b]furans from 2,3-dihalophenols |
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Authors: | Sanz Roberto Castroviejo M Pilar Fernández Yolanda Fañanás Francisco J |
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Institution: | Departamento de Química, Area de Química Orgánica, Facultad de Ciencias, Universidad de Burgos, Pza. Missael Ba?uelos s/n, 09001-Burgos, Spain. rsd@ubu.es |
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Abstract: | Tandem Sonogashira coupling/5-endo-dig cyclization reactions on 2,3-dihalophenols suppose a straightforward entry to 4-halobenzob]furans, which can be easily transformed into 4-functionalized benzob]furans, that are difficult to synthesize by other procedures. On the other hand, the starting 2,3-dihalophenols are efficiently prepared from commercially available 3-halophenols, via their N,N-diethyl carbamates by selective lithiation at the 2-positions by treatment with s-BuLi/TMEDA or LDA at low temperature and reaction with halogen electrophilic reagents. |
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