Ambient Temperature Cleavages of Amides in an Aqueous Medium for the Ipsilateral Effect of 1,8-Substituents on Naphthalene.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-20 DOI:10.1021/acs.orglett.5c00122

Lunyu Ou, Hongyun Li, Weifeng Wang, Yufen Zhao, Hua Fu

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Abstract

The selective release of a molecule in its native form from a constructed framework is very attractive in the chemical and biological fields. The amide bond is ubiquitous in biological and chemical systems. However, the cleavage of an unmodified typical amide is a great challenge because of its high level of stabilization. Here, couplings of 8-azido-1-naphthoic acid prepared by us with amines afforded 8-azido-1-naphthamides. Reductions of 8-azido in 8-azido-1-naphthamides with sodium sulfide yielded 8-amino-1-naphthamides, and then, fast intramolecular nucleophilic attack of 8-amino to carbonyl of 1-amido in the presence of silica gel as the additive afforded 2,3-benzo[cd]indol-2(1H)-one freeing amines in almost quantitative conversion rates for the ipsilateral effect of 1,8-substituents on naphthalene. Furthermore, this strategy was extended to the cleavages of esters (alkyl 8-azido-1-naphthoates) successfully. The cleavages of amides and esters were performed in an aqueous medium at room temperature with wide functional group tolerance and were suitable for gram-scale production.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

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.