One-Pot (3 + 2) Cycloaddition-Isomerization-Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives.
Journal
The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R
Informations de publication
Date de publication:
04 Aug 2023
04 Aug 2023
Historique:
medline:
21
7
2023
pubmed:
21
7
2023
entrez:
21
7
2023
Statut:
ppublish
Résumé
A facile access to 5-aryl-3-trifluoromethylpyrazoles has been developed by a one-pot (3 + 2) cycloaddition-isomerization-oxidation sequence employing 2,2,2-trifluorodiazoethane and styryl derivatives. A broad variety of functional groups and good yields are achieved under mild conditions. Additionally, the functionalization of 3-trifluoromethylpyrazoles was studied. DFT calculations of the cycloaddition transition state energies are consistent with the experimentally observed reactivity.
Identifiants
pubmed: 37478336
doi: 10.1021/acs.joc.3c00396
pmc: PMC10407847
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11258-11262Références
Chemistry. 2014 Apr 22;20(17):4942-7
pubmed: 24700600
Angew Chem Int Ed Engl. 2013 Jun 10;52(24):6255-8
pubmed: 23616303
Chem Rev. 2020 Nov 25;120(22):12718-12755
pubmed: 32940457
J Agric Food Chem. 2020 Mar 11;68(10):3071-3078
pubmed: 32078770
Org Lett. 2021 Aug 6;23(15):6062-6066
pubmed: 34319752
Org Lett. 2014 Jun 6;16(11):3122-5
pubmed: 24850209
Eur J Med Chem. 2015 Jun 5;97:786-815
pubmed: 25555743
Dalton Trans. 2015 Dec 28;44(48):21109-23
pubmed: 26596893
J Med Chem. 1997 Apr 25;40(9):1347-65
pubmed: 9135032
Org Lett. 2020 Feb 7;22(3):809-813
pubmed: 31951135
Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4569-4574
pubmed: 28328171
Org Lett. 2022 Apr 8;24(13):2499-2503
pubmed: 35343703
Org Biomol Chem. 2022 Nov 23;20(45):8787-8817
pubmed: 36331498
J Org Chem. 2021 Feb 5;86(3):2385-2405
pubmed: 33423495
BMC Vet Res. 2014 Sep 05;10:184
pubmed: 25190452
J Am Chem Soc. 2017 Apr 19;139(15):5293-5296
pubmed: 28366001
Chem Rev. 2021 Feb 10;121(3):1670-1715
pubmed: 33382252
Org Lett. 2020 Mar 6;22(5):2012-2016
pubmed: 32073866
Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1101-4
pubmed: 21268204
Org Lett. 2022 Mar 25;24(11):2258-2263
pubmed: 35297254
Angew Chem Int Ed Engl. 2010;49(5):938-41
pubmed: 20039242
J Cancer Res Clin Oncol. 2006 Apr;132(4):223-33
pubmed: 16362334
J Am Chem Soc. 2020 Aug 12;142(32):13846-13855
pubmed: 32668150
J Org Chem. 2017 Jul 21;82(14):7200-7214
pubmed: 28625049
RSC Med Chem. 2022 Aug 26;13(11):1300-1321
pubmed: 36439976
Angew Chem Int Ed Engl. 2017 Jul 17;56(30):8823-8827
pubmed: 28544160