Next Article in Journal
Novel Pyrazolo[3,4-d]pyrimidine Derivatives as Potential Antitumor Agents: Exploratory Synthesis, Preliminary Structure-Activity Relationships, and in Vitro Biological Evaluation
Previous Article in Journal
Resin Diterpenes from Austrocedrus chilensis
Molecules 2011, 16(12), 10668-10684; doi:10.3390/molecules161210668
Article

Microwave-Assisted Synthesis of New N1,N4-Substituted Thiosemicarbazones

1, 1, 1, 2 and 1,*
1 Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, 23890-000, Seropédica, Rio de Janeiro, Brazil 2 Departamento de Micologia, Instituto Oswaldo Cruz – FIOCRUZ, 21045-900, Rio de Janeiro, Rio de Janeiro, Brazil
* Author to whom correspondence should be addressed.
Received: 5 October 2011 / Revised: 6 December 2011 / Accepted: 16 December 2011 / Published: 20 December 2011
Download PDF [257 KB, uploaded 18 June 2014]

Abstract

We present an efficient procedure for the synthesis of thirty-six N1,N4-substituted thiosemicarbazones, including twenty-five ones that are reported for the first time, using a microwave-assisted methodology for the reaction of thiosemicarbazide intermediates with aldehydes in the presence of glacial acetic acid in ethanol and under solvent free conditions. Overall reaction times (20–40 min when ethanol as solvent, and 3 min under solvent free conditions) were much shorter than with the traditional procedure (480 min); satisfactory yields and high-purity compounds were obtained. The thiosemicarbazide intermediates were obtained from alkyl or aryl isothiocyanates and hydrazine hydrate or phenyl hydrazine by stirring at room temperature for 60 min or by microwave irradiation for 30 min, with lower yields for the latter. The preliminary in vitro antifungal activity of thiosemicarbazones was evaluated against Aspergillus parasiticus and Candida albicans.
Keywords: thiosemicarbazone; thiosemicarbazide; microwave irradiation; antifungal activity thiosemicarbazone; thiosemicarbazide; microwave irradiation; antifungal activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Reis, C.M.; Pereira, D.S.; Paiva, R.O.; Kneipp, L.F.; Echevarria, A. Microwave-Assisted Synthesis of New N1,N4-Substituted Thiosemicarbazones. Molecules 2011, 16, 10668-10684.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert