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2. Exploration of fluoral hydrazones derived from carbohydrazides for the synthesis of trifluoromethylated heterocycles

Author

Katarzyna Urbaniak, Heinz Heimgartner, Grzegorz Mlostoń, Anthony Linden, Natalia Jacaszek, University of Zurich, and Mlostoń, Grzegorz

Subjects
Pharmacology, 10120 Department of Chemistry, 1602 Analytical Chemistry, Fluoral hydrate, Organic Chemistry, Molecular sieve, Analytical Chemistry, Mercaptoacetic acid, chemistry.chemical_compound, Acetic anhydride, 3004 Pharmacology, chemistry, 540 Chemistry, Organic chemistry, Methanol, Benzene, 1605 Organic Chemistry
Abstract

The reaction of fluoral hydrate with carbohydrazides in methanol in the presence of molecular sieves (4 A) gave the desired N-acylated fluoral hydrazones (3a–f) in fair yields. Treatment of the latter with mercaptoacetic acid in benzene led to the corresponding 2-trifluoromethyl-1,3-thiazolidinone derivatives (4a–f), whereas the reaction with acetic anhydride gave 3-acetyl-2,3-dihydro-2-trifluoromethyl-1,3,4-oxadiazoles (5a–f). The structures of each type of product have been established by X-ray crystallography.

Published
2014

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