Spiroannulation of Oxindoles via Aryne and Alkyne Incorporation: Substituent-Diverted, Transition-Metal-Free, One-Pot Access to Spirooxindoles
- PMID: 28573864
- DOI: 10.1021/acs.orglett.7b01233
Spiroannulation of Oxindoles via Aryne and Alkyne Incorporation: Substituent-Diverted, Transition-Metal-Free, One-Pot Access to Spirooxindoles
Abstract
A "product control via substrate design" strategy has been conceptualized and implemented to harness the potential of aryne and activated alkyne insertions into oxindoles to readily and efficiently furnish pharmacophoric indano- and cyclopentannulated spirooxindole scaffolds in an operationally straightforward, one-pot, transition-metal-free protocol.
Similar articles
-
Transition-Metal-Free Cyclization of Propargylic Alcohols with Aryne: Synthesis of 3-Benzofuranyl-2-oxindole and 3-Spirooxindole Benzofuran Derivatives ⊥.Org Lett. 2018 Jul 6;20(13):3824-3828. doi: 10.1021/acs.orglett.8b01414. Epub 2018 Jun 19. Org Lett. 2018. PMID: 29920110
-
Stitching Oxindoles and Ynones in a Domino Process: Access to Spirooxindoles and Application to a Short Synthesis of Spindomycin B.Org Lett. 2017 Nov 17;19(22):6152-6155. doi: 10.1021/acs.orglett.7b03030. Epub 2017 Oct 30. Org Lett. 2017. PMID: 29148813
-
Metal- and Oxidant-Free Modular Approach To Access N-Alkoxy Oxindoles via Aryne Annulation.Org Lett. 2018 Aug 17;20(16):4848-4853. doi: 10.1021/acs.orglett.8b01972. Epub 2018 Jul 25. Org Lett. 2018. PMID: 30044101
-
Enantioselective synthesis of substituted oxindoles and spirooxindoles with applications in drug discovery.Curr Opin Drug Discov Devel. 2010;13(6):758-76. Curr Opin Drug Discov Devel. 2010. PMID: 21061236 Review.
-
Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.Mol Divers. 2016 Feb;20(1):185-232. doi: 10.1007/s11030-015-9596-0. Epub 2015 Jun 9. Mol Divers. 2016. PMID: 26055184 Review.
Cited by
-
Isatin Bis-Indole and Bis-Imidazothiazole Hybrids: Synthesis and Antimicrobial Activity.Molecules. 2022 Sep 7;27(18):5781. doi: 10.3390/molecules27185781. Molecules. 2022. PMID: 36144518 Free PMC article.
-
Palladium-catalysed 5-endo-trig allylic (hetero)arylation.Chem Sci. 2020 Apr 30;11(19):4948-4953. doi: 10.1039/d0sc01932a. Chem Sci. 2020. PMID: 34122951 Free PMC article.
-
Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.Beilstein J Org Chem. 2018 Apr 18;14:875-883. doi: 10.3762/bjoc.14.74. eCollection 2018. Beilstein J Org Chem. 2018. PMID: 29765468 Free PMC article.
Publication types
LinkOut - more resources
Full Text Sources
Other Literature Sources