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Preparation of 4-Diazoisoquinolin-3-ones via Dimroth Rearrangement and Their Extension to 4-Aryltetrahydroisoquinolin-3-ones.

4-Diazoisoquinolin-3-ones were prepared efficiently via TBAB-promoted rearrangement of 4-diazoisochroman-3-imines under mild reaction conditions. The resulted 4-diazoisoquinolin-3-ones could be conveniently applied for the synthesis of 4-aryltetrahydroisoquinolin-3-ones either by the TfOH-catalyzed reaction… Click to show full abstract

4-Diazoisoquinolin-3-ones were prepared efficiently via TBAB-promoted rearrangement of 4-diazoisochroman-3-imines under mild reaction conditions. The resulted 4-diazoisoquinolin-3-ones could be conveniently applied for the synthesis of 4-aryltetrahydroisoquinolin-3-ones either by the TfOH-catalyzed reaction with electron-rich arenes or by the BF3-promoted reaction with aryl aldehydes.

Keywords: diazoisoquinolin ones; ones via; aryltetrahydroisoquinolin ones; preparation diazoisoquinolin

Journal Title: Organic letters
Year Published: 2019

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