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Synthesis 2023; 55(01): 141-149
DOI: 10.1055/a-1930-6840
paper

Preparation of 4-Arylthiazol-2(3H)-ones and the Three-Component Synthesis of Multidentate 5,5′-Methylenebis[4-arylthiazol-2(3H)-one] Ligands

Juan F. Ortuño
a   University of Alicante, Department of Organic Chemistry, Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Instituto de Síntesis Orgánica (ISO), PO Box 99, 03080 Alicante, Spain
b   Medalchemy, S. L. Ancha de Castelar, 46-48, entlo. A. San Vicente del Raspeig, 03690 Alicante, Spain
,
Samet Poyraz
c   Department of Basic Pharmaceutical Sciences, Faculty of Pharmacy, Çukurova University, Balcalı 01330, Adana, Turkey
,
Asmaa Belabbes
a   University of Alicante, Department of Organic Chemistry, Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Instituto de Síntesis Orgánica (ISO), PO Box 99, 03080 Alicante, Spain
,
Özge Kavas
d   Department of Chemistry, Bolu Abant İzzet Baysal University, 14280 Bolu, Turkey
,
Samet Belveren
e   Department of Chemistry, Faculty of Pharmacy, Mersin University, Yenisehir, 33169 Mersin, Turkey
,
Cevher Altuğ
d   Department of Chemistry, Bolu Abant İzzet Baysal University, 14280 Bolu, Turkey
,
María de Gracia Retamosa
a   University of Alicante, Department of Organic Chemistry, Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Instituto de Síntesis Orgánica (ISO), PO Box 99, 03080 Alicante, Spain
,
Francisco Foubelo 
a   University of Alicante, Department of Organic Chemistry, Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Instituto de Síntesis Orgánica (ISO), PO Box 99, 03080 Alicante, Spain
,
Christopher M. Pask
f   School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK
,
José M. Sansano 
a   University of Alicante, Department of Organic Chemistry, Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Instituto de Síntesis Orgánica (ISO), PO Box 99, 03080 Alicante, Spain
,
H. Ali Döndaş  ∗
c   Department of Basic Pharmaceutical Sciences, Faculty of Pharmacy, Çukurova University, Balcalı 01330, Adana, Turkey
g   Department of Biotechnology, Institute of Natural and Applied Sciences, Çukurova University, Balcalı 01330, Adana, Turkey
› Author AffiliationsWe gratefully acknowledge financial support from Çukurova University (Project no: TSA-2021-13814), Mersin University (Project no. 2020-1-AP4-3982), and by the University of Alicante (VIGROB-068, UAUSTI21-05). We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (project RED2018-102387-T), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo ­Europeo de Desarrollo Regional (FEDER, EU) (project PID2019-107268GB-I00), and the Generalitat Valenciana (IDIFEDER/2021/013, CIDEGENT/2020/058).
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Abstract

The synthesis of 4-arylthiazol-2(3H)-ones is reported employing a novel and mild methodology using benign solvents. In a second objective, the multicomponent preparation of 5,5′-methylenebis[4-arylthiazol-2(3H)-ones] is described following the same strategy. The analysis of the mechanism is also studied and confirmed using chemical tests.

Key words

thiazolones - methylenebis(thiazolones) - multicomponent - multidentated - ligand

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/ a-1930-6840.
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Publication History

Received: 16 May 2022

Accepted after revision: 25 August 2022

Accepted Manuscript online:
25 August 2022

Article published online:
29 September 2022

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