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New crown compounds containing a 1,3,4-thiadiazole moiety: Synthesis and crystal structure

✍ Scribed by Moha Outirite; Fouad Bentiss; Mounim Lebrini; Jean-Pierre Wignacourt; Michel Lagrenée

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
101 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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The syntheses of new macrocyclic compounds are described. The 2,5‐bis(hydroxyphenyl)‐1,3,4‐thiadiazole reacts with allyl bromide to give the corresponding allyloxy derivative. The allyl is used to functionalize the ortho position by means of a Claisen rearrangement under microwave irradiation. New 2,5‐dihydroxyphenyl‐1,3,4‐thiadiazoles are obtained, which are converted into macrocyclic polyethers. The structures of the new macrocyclic compounds were confirmed by ^1^H, ^13^C NMR, and mass spectroscopy. The crystal structure of 2,5‐bis(2‐allyloxyphenyl)‐1,3,4‐thiadiazole has been determined. J. Heterocyclic Chem., (2009).

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