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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

✍ Scribed by Albert Lévai; Tamás Patonay

Publisher: Journal of Heterocyclic Chemistry
Year: 1999
Tongue: English
Weight: 580 KB
Volume: 36
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570360328

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✦ Synopsis

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‐1__H__‐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.

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