Issue 3, 2014
From the journal:

RSC Advances

Microwave-activated synthesis of thiazolo[5,4-d]thiazoles by a condensation/oxidation sequence†‡

Alessio Dessì,ab   Massimo Calamante,ab   Alessandro Mordini,ab   Lorenzo Zani,bc   Maurizio Taddeid  and  Gianna Reginato*b  

* Corresponding authors

a Università degli Studi di Firenze, Dipartimento di Chimica “Ugo Schiff”, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy

b CNR – Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy
E-mail: gianna.reginato@iccom.cnr.it
Fax: +39 044 5225203
Tel: +39 055 5225255

c CNR – Istituto per la Sintesi Organica e la Fotoreattività (CNR-ISOF), Via Piero Gobetti 101, 40129 Bologna, Italy

d Università degli Studi di Siena, Dipartimento di Biotecnologie, Chimica e Farmacia, Via A. Moro 2, 53100 Siena, Italy

Abstract

A microwave-assisted preparation of symmetrical thiazolo[5,4-d]thiazoles from the corresponding aldehydes is presented. The two-step reaction sequence comprises the condensation of aldehydes with dithiooxamide followed by oxidation/aromatization with 1,4-benzoquinone derivatives. The new procedure provides the desired products in good yields and in most cases allows reduction of the excess of aldehyde employed in the process compared to previous methodologies. For the first time, application of the reaction both on aromatic and aliphatic aldehydes is demonstrated.

Graphical abstract: Microwave-activated synthesis of thiazolo[5,4-d]thiazoles by a condensation/oxidation sequence

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Article information

DOI
https://doi.org/10.1039/C3RA45015E
Article type
Paper
Submitted
11 Sep 2013
Accepted
23 Oct 2013
First published
24 Oct 2013

RSC Adv., 2014,4, 1322-1328

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Microwave-activated synthesis of thiazolo[5,4-d]thiazoles by a condensation/oxidation sequence

A. Dessì, M. Calamante, A. Mordini, L. Zani, M. Taddei and G. Reginato, RSC Adv., 2014, 4, 1322 DOI: 10.1039/C3RA45015E

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