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Schwartz's Reagent-Mediated Regiospecific Synthesis of 2,3-Disubstituted Indoles from Isatins.
Org Lett. 2016 Jan 15; 18(2):149-51.OL

Abstract

An expeditious, functional group-tolerant synthesis of indoles from isatins is described. Isatins are treated with Grignard reagents to yield oxindoles. These, in turn, are reduced with Schwartz's reagent and subjected to nucleophile addition and dehydration to yield 2,3-disubstituted indoles regiospecifically. This represents a divergent approach to the synthesis of these medicinally and synthetically important compounds.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ulikowski A
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Furman B
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.

MeSH

CatalysisIndolesIsatinMolecular StructureOrganometallic CompoundsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26695735

Citation

Ulikowski, A, and B Furman. "Schwartz's Reagent-Mediated Regiospecific Synthesis of 2,3-Disubstituted Indoles From Isatins." Organic Letters, vol. 18, no. 2, 2016, pp. 149-51.
Ulikowski A, Furman B. Schwartz's Reagent-Mediated Regiospecific Synthesis of 2,3-Disubstituted Indoles from Isatins. Org Lett. 2016;18(2):149-51.
Ulikowski, A., & Furman, B. (2016). Schwartz's Reagent-Mediated Regiospecific Synthesis of 2,3-Disubstituted Indoles from Isatins. Organic Letters, 18(2), 149-51. https://doi.org/10.1021/acs.orglett.5b03449
Ulikowski A, Furman B. Schwartz's Reagent-Mediated Regiospecific Synthesis of 2,3-Disubstituted Indoles From Isatins. Org Lett. 2016 Jan 15;18(2):149-51. PubMed PMID: 26695735.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Schwartz's Reagent-Mediated Regiospecific Synthesis of 2,3-Disubstituted Indoles from Isatins. AU - Ulikowski,A, AU - Furman,B, Y1 - 2015/12/22/ PY - 2015/12/24/entrez PY - 2015/12/24/pubmed PY - 2016/6/4/medline SP - 149 EP - 51 JF - Organic letters JO - Org Lett VL - 18 IS - 2 N2 - An expeditious, functional group-tolerant synthesis of indoles from isatins is described. Isatins are treated with Grignard reagents to yield oxindoles. These, in turn, are reduced with Schwartz's reagent and subjected to nucleophile addition and dehydration to yield 2,3-disubstituted indoles regiospecifically. This represents a divergent approach to the synthesis of these medicinally and synthetically important compounds. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26695735/Schwartz's_Reagent_Mediated_Regiospecific_Synthesis_of_23_Disubstituted_Indoles_from_Isatins_ DB - PRIME DP - Unbound Medicine ER -