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Paper | Special issue | Vol 88, No. 1, 2014, pp.387-401
Published online, 19th July, 2013
DOI: 10.3987/COM-13-S(S)40
Exploration of Fluoral Hydrazones Derived from Carbohydrazides for the Synthesis of Trifluoromethylated Heterocycles

Grzegorz Mlostoń,* Katarzyna Urbaniak, Natalia Jacaszek, Anthony Linden, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


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