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.

中文翻译：

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酰胺对萘的 Staudinger 裂解对 1,8-取代基的同侧效应


精心制备了 8-（叠氮甲基）-1-萘甲酸，它与胺的偶联提供了相应的 8-（叠氮甲基）-1-萘酰胺。8-（叠氮甲基）-1-萘酰胺与膦的 Staudinger 反应产生了亚氨基腈烷，亚氨基腈烷的易分子内环化得到了 2,3-二氢-1H-苯并[去]异喹啉-1-酮，使胺具有几乎定量的转化率，用于 1,8-取代基对萘的同侧作用。该方案具有一些优点，包括现成的保护基团、以近乎定量的转化率切割酰胺、水性介质、室温反应、广泛的底物范围、广泛的官能团耐受性和合适的放大反应。