Ultrasound-Promoted Synthesis of Spirocyclopropanes from Switchable Starting Materials via Azomethine Ylide [3+2]-Cycloaddition

Issa Yavari; Sara Sheikhi; Jamil Sheykhahmadi; Zohreh Taheri; Mohammad Reza Halvagar

doi:10.1055/a-1370-1884

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(12): 2057-2066
DOI: 10.1055/a-1370-1884

paper

Ultrasound-Promoted Synthesis of Spirocyclopropanes from Switchable Starting Materials via Azomethine Ylide [3+2]-Cycloaddition

Issa Yavari ∗

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

,

Sara Sheikhi

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

,

Jamil Sheykhahmadi

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

,

Zohreh Taheri

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

,

Mohammad Reza Halvagar

^bDepartment of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran

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Abstract

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Abstract

An ultrasound-promoted green protocol to access a new series of spirocyclopropanes from indeno[1,2-b]quinoxaline derivatives and azomethine ylides, generated in situ from the iodine-catalyzed reaction of acetophenones as well as of 2-methylquinoline with pyridine in the presence of a base, is described. These transformations proceed via a spirocyclopropanation reaction followed by elimination of pyridine. Clear evidence for the structure of a spirocyclopropane-linked indenoquinoxaline derivative was obtained from single-crystal X-ray analysis. The most important feature of this reaction is the fact it forms three stereogenic centers, one of which is quaternary, with excellent selectivity.

Key words

sonochemical synthesis - [3+2]-cycloaddition - spirocyclopropanes - azomethine ylides - iodine

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