Reaction of E-2-arylidene-1-indanones, Z-aurones, Z-1-thioaurones and Z- 2-arylidene-2,3-dihydro-1H-indol-3-ones with diazomethane

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Abstract

1,3-Dipolar cycloaddition of E-2-arylidene-1-indanones 1a-h and Z- aurones 3a-c with diazomethane provided trans-spiro-1-pyrazolines 2a-h and 4a-c, respectively, as sole products. However, the same cycloaddition of Z- 1-thioaurones 5a-f afforded a mixture of Z-α-methyl-1-thioaurones 6a-f and trans-cyclopropane derivatives 7a-f as a result of the spontaneous denitrogenation of the initially formed 1-pyrazolines. Similar reaction of Z- 2-arylidene-2,3-dihydro-1H-indol-3-ones 8a,b and diazomethane yielded trans- cyclopropanes 9a,b. Structure and stereochemistry of the compounds synthesized have been elucidated by nmr spectroscopic measurements.

Original languageEnglish
Pages (from-to)747-753
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume36
Issue number3
DOIs
Publication statusPublished - Jan 1 1999

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ASJC Scopus subject areas

  • Organic Chemistry

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