Journal
ORGANIC LETTERS
Volume 23, Issue 16, Pages 6578-6582Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02416
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Funding
- National Natural Science Foundation of China [22078192, 81973453]
- Fund for Scientific Research-Flanders-FWO (Belgium)
- RUDN University Strategic Academic Leadership Program
- China Scholarship Council (CSC)
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An efficient palladium-catalyzed reaction under microwave irradiation has been developed for the construction of 4-substituted isoquinolines through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade. The practical value of this method was demonstrated by conducting millimole-scale reactions and transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue.
An efficient palladium-catalyzed reaction of N-propargyl oxazolidines for the construction of 4-substituted isoquinolines under microwave irradiation is developed. This transformation proceeds through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade via C-O and C-N bond cleavages of the oxazolidine ring. The practical value of this method has also been explored by conducting a millimole-scale reaction, as well as by transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue.
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