Lunyu Ou, Zhengyi Yi, Yue Zhang, Yufen Zhao, Hua Fu
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Staudinger Cleavages of Amides on Naphthalene for the Ipsilateral Effect of 1,8-Substituents
8-(Azidomethyl)-1-naphthoic acid was elaborately prepared, and its coupling with amines provided the corresponding 8-(azidomethyl)-1-naphthamides. The Staudinger reactions of 8-(azidomethyl)-1-naphthamides with phosphine produced iminophosphoranes, and easy intramolecular cyclization of the iminophosphoranes afforded 2,3-dihydro-1H-benzo[de]isoquinolin-1-one leaving amines with almost quantitative conversion rates for the ipsilateral effect of 1,8-substituents on naphthalene. The protocol exhibits some advantages, including a readily available protecting group, cleavages of amides in almost quantitative conversion rates, an aqueous medium, reactions at room temperature, a broad substrate scope, wide functional group tolerance, and suitable scale-up reactions.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.