Mechanochemistry Frees Thiourea Dioxide (TDO) from the 'Veils' of Solvent, Exposing All Its Reactivity.

TDO heterocycles mechanochemistry thiourea dioxide

Journal

Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009

Informations de publication

Date de publication:
28 Feb 2023
Historique:
received: 31 01 2023
revised: 24 02 2023
accepted: 25 02 2023
entrez: 11 3 2023
pubmed: 12 3 2023
medline: 12 3 2023
Statut: epublish

Résumé

The synthesis of nitrogen-based heterocycles has always been considered essential in developing pharmaceuticals in medicine and agriculture. This explains why various synthetic approaches have been proposed in recent decades. However performing as methods, they often imply harsh conditions or the employment of toxic solvents and dangerous reagents. Mechanochemistry is undoubtedly one of the most promising technologies currently used for reducing any possible environmental impact, addressing the worldwide interest in counteracting environmental pollution. Following this line, we propose a new mechanochemical protocol for synthesizing various heterocyclic classes by exploiting thiourea dioxide (TDO)'s reducing proprieties and electrophilic nature. Simultaneously exploiting the low cost of a component of the textile industry such as TDO and all the advantages brought by a green technique such as mechanochemistry, we plot a route towards a more sustainable and eco-friendly methodology for preparing heterocyclic moieties.

Identifiants

pubmed: 36903485
pii: molecules28052239
doi: 10.3390/molecules28052239
pmc: PMC10005452
pii:
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Subventions

Organisme : Ministry of Education, Universities and Research
ID : PRIN 2017 project (grant number: 2017B7MMJ5_001) "MultIFunctional polymer cOmposites based on groWn matERials (MIFLOWER)
Organisme : Fondazione Banco di Sardegna
ID : FdS, F72F20000230007

Références

Chem Sci. 2018 Mar 7;9(12):3080-3094
pubmed: 29780455
J Org Chem. 2020 Nov 6;85(21):13906-13919
pubmed: 33085479
J Org Chem. 2012 Aug 3;77(15):6653-6
pubmed: 22808946
RSC Adv. 2020 Apr 20;10(26):15461-15492
pubmed: 35558641
Bioorg Med Chem. 2006 Oct 15;14(20):7051-61
pubmed: 16798000
Eur J Med Chem. 2007 Nov-Dec;42(11-12):1334-57
pubmed: 17433505
Adv Mater. 2019 Mar;31(11):e1808341
pubmed: 30672034
Org Lett. 2016 Dec 16;18(24):6316-6319
pubmed: 27978659
Cell Death Dis. 2015 Mar 12;6:e1686
pubmed: 25766325
J Am Chem Soc. 2015 Feb 25;137(7):2476-9
pubmed: 25668586
Chem Res Toxicol. 1988 May-Jun;1(3):169-74
pubmed: 2979727
ACS Chem Neurosci. 2021 Apr 7;12(7):1072-1092
pubmed: 33760580
Org Lett. 2020 May 15;22(10):3789-3793
pubmed: 32362124
Bioorg Med Chem. 2015 Sep 15;23(18):6087-99
pubmed: 26314922
Immune Netw. 2020 Aug 04;20(4):e29
pubmed: 32895616
J Am Chem Soc. 2013 May 1;135(17):6384-7
pubmed: 23560524
RSC Med Chem. 2022 Sep 8;13(10):1150-1196
pubmed: 36325400
J Phys Chem B. 2005 Sep 15;109(36):17281-9
pubmed: 16853206
BMC Chem. 2019 May 15;13(1):66
pubmed: 31384813
Eur J Med Chem. 2014 Apr 9;76:494-505
pubmed: 24602792
Arzneimittelforschung. 1997 Jul;47(7):834-6
pubmed: 9272240
Chem Commun (Camb). 2021 Feb 2;57(9):1080-1092
pubmed: 33438694
Phys Chem Chem Phys. 2015 Jun 14;17(22):15012-8
pubmed: 25989446
J Hazard Mater. 2023 Mar 5;445:130558
pubmed: 36495641
Arch Pharm (Weinheim). 2017 Jun;350(6):
pubmed: 28544162
Chem Commun (Camb). 2014 Jul 18;50(56):7469-72
pubmed: 24875017
Int J Mol Sci. 2020 Dec 14;21(24):
pubmed: 33327584
ChemSusChem. 2022 Sep 7;15(17):e202200362
pubmed: 35867602
J Med Chem. 2015 Jul 23;58(14):5419-36
pubmed: 26111355
Environ Pollut. 2018 Aug;239:512-521
pubmed: 29684878
Yakugaku Zasshi. 1977 Nov;97(11):1253-6
pubmed: 616828
ACS Med Chem Lett. 2017 Mar 31;8(5):543-548
pubmed: 28523108
Dalton Trans. 2018 Sep 11;47(35):12353-12361
pubmed: 30118118
Chem Rev. 2019 Feb 27;119(4):2611-2680
pubmed: 30516963
Chemistry. 2014 Oct 27;20(44):14164-76
pubmed: 25265917
J Biomol Struct Dyn. 2023 Mar;41(5):1798-1810
pubmed: 35000553
Inorg Chem. 2016 May 16;55(10):4795-805
pubmed: 27145140
Beilstein J Org Chem. 2017 Sep 11;13:1907-1931
pubmed: 29062410
J Org Chem. 1976 Oct 29;41(22):3624-5
pubmed: 978305
J Org Chem. 2016 May 20;81(10):4122-33
pubmed: 27111189
Bioorg Chem. 2019 Oct;91:103131
pubmed: 31377387
Appl Spectrosc. 2014;68(12):1327-32
pubmed: 25357155
J Org Chem. 2018 Aug 17;83(16):9553-9560
pubmed: 29993244
Beilstein J Org Chem. 2019 Apr 12;15:881-900
pubmed: 31019581
J Org Chem. 2015 Feb 6;80(3):1644-50
pubmed: 25588127
Org Biomol Chem. 2011 Oct 21;9(20):6943-8
pubmed: 21881671
ACS Cent Sci. 2017 Jan 25;3(1):13-19
pubmed: 28149948
Chem Soc Rev. 2019 Apr 15;48(8):2274-2292
pubmed: 30806391
Angew Chem Int Ed Engl. 2018 Dec 3;57(49):16104-16108
pubmed: 30335216
J Org Chem. 2019 Jan 4;84(1):104-119
pubmed: 30540185

Auteurs

Francesco Basoccu (F)

Department of Chemical and Geological Sciences, University of Cagliari, 09042 Monserrato, Italy.

Federico Cuccu (F)

Department of Chemical and Geological Sciences, University of Cagliari, 09042 Monserrato, Italy.

Pietro Caboni (P)

Department of Chemical and Geological Sciences, University of Cagliari, 09042 Monserrato, Italy.

Lidia De Luca (L)

Department of Chemical, Physical, Mathematical, and Natural Sciences, University of Sassari, Via Vienna 2, 07100 Sassari, Italy.

Andrea Porcheddu (A)

Department of Chemical and Geological Sciences, University of Cagliari, 09042 Monserrato, Italy.

Classifications MeSH