Brønsted Acid Catalyzed Direct Annulation of Alkoxyallenes and Naphthols to Chroman Ketals

Maosheng He; Jinlong Zhang; Cong Zhang; Hao-Yang Wang; Gaoxi Jiang

doi:10.1055/s-0040-1719892

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(09): 2148-2156
DOI: 10.1055/s-0040-1719892

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Brønsted Acid Catalyzed Direct Annulation of Alkoxyallenes and Naphthols to Chroman Ketals

Maosheng He

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Jinlong Zhang

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

,

Cong Zhang∗

^cInstitute of Advanced Materials, Key Laboratory of Flexible Electronics, Nanjing Tech University, Dingjiaqiao Campus, XinMoFanMaLu No. 5, 210000 Nanjing, P. R. of China

,

Hao-Yang Wang

^dLaboratory of Mass Spectrometry Analysis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

,

Gaoxi Jiang∗

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

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Abstract

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Abstract

A straightforward Brønsted acid-catalyzed and scalable annulation of alkoxyallenes with simple naphthols was developed, affording chroman ketals in 49–84% yields. The versatile chroman ketals can be easily converted into coumarins by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidation, and a series of 2-substituted chromans via nucleophilic substitutions.

Key words

Brønsted acids - annulation - chroman ketal - coumarin - chroman

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Referenzen

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