Header

UZH-Logo

Maintenance Infos

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


Mloston, Grzegorz; Urbaniak, Katarzyna; Jacaszek, Natalia; Linden, Anthony; Heimgartner, Heinz (2014). Exploration of fluoral hydrazones derived from carbohydrazides for the synthesis of trifluoromethylated heterocycles. Heterocycles, 88(1):387-401.

Abstract

The reaction of fluoral hydrate with carbohydrazides in methanol in the presence of molecular sieves (4 Å) 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.

Abstract

The reaction of fluoral hydrate with carbohydrazides in methanol in the presence of molecular sieves (4 Å) 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.

Statistics

Citations

Dimensions.ai Metrics
7 citations in Web of Science®
7 citations in Scopus®
8 citations in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

163 downloads since deposited on 19 Aug 2013
9 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:19 Aug 2013 06:37
Last Modified:14 Feb 2018 20:48
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
OA Status:Green
Publisher DOI:https://doi.org/10.3987/COM-13-S(S)40

Download

Download PDF  'Exploration of fluoral hydrazones derived from carbohydrazides for the synthesis of trifluoromethylated heterocycles'.
Preview
Content: Published Version
Language: English
Filetype: PDF
Size: 883kB
View at publisher