2023
DOI: 10.1021/acs.joc.3c01142
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Palladium-Catalyzed Tandem C(sp3)-H Insertion Cyclization of 2-(2-Vinylarene)acetonitriles with Isocyanides to Access Naphthalen-2-amines

Abstract: A Pd-catalyzed cyclization reaction of 2-(2vinylarene)acetonitriles and isocyanides has been documented. Various naphthalen-2-amines were obtained in moderate to good yields under mild conditions. The in vitro cytotoxicity of all products was evaluated by MTT assay against seven human cancer cell lines. The results indicated that compounds 3ea, 3ma, and 3ob exhibited effective anticancer activities against the tested cancer cells.

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“… The utility of aminonaphthalene derivatives underscores the importance of developing new and efficient synthetic methodologies for their preparation. Despite their utility, synthetic routes to 1-aminonaphthalene derivatives are limited and suffer from poor functional group tolerance, a requirement for precious metal catalysts or nontrivial precursors, limited substrate scope, and/or undesired N-alkylation. Given these drawbacks, we sought to develop a simple and efficient synthetic route to 1-aminonaphthalenes from abundant and inexpensive starting materials. Here we describe a two-step route to 1-aminonaphthalene derivatives from readily available benzaldehydes.…”
mentioning
confidence: 99%
“… The utility of aminonaphthalene derivatives underscores the importance of developing new and efficient synthetic methodologies for their preparation. Despite their utility, synthetic routes to 1-aminonaphthalene derivatives are limited and suffer from poor functional group tolerance, a requirement for precious metal catalysts or nontrivial precursors, limited substrate scope, and/or undesired N-alkylation. Given these drawbacks, we sought to develop a simple and efficient synthetic route to 1-aminonaphthalenes from abundant and inexpensive starting materials. Here we describe a two-step route to 1-aminonaphthalene derivatives from readily available benzaldehydes.…”
mentioning
confidence: 99%