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

6 citations in Web of Science®
6 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

155 downloads since deposited on 19 Aug 2013
20 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:05 Apr 2016 16:54
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Publisher DOI:https://doi.org/10.3987/COM-13-S(S)40

Download

Preview Icon on Download
Preview
Content: Published Version
Language: English
Filetype: PDF
Size: 883kB
View at publisher

Article Networks

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations