EurekaMag.com logo
+ Site Statistics
References:
52,725,316
Abstracts:
28,411,598
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Regioselective synthesis of 4- and 7-alkoxyindoles from 2,3-dihalophenols: application to the preparation of indole inhibitors of phospholipase A2


Journal of Organic Chemistry 72(14): 5113-5118
Regioselective synthesis of 4- and 7-alkoxyindoles from 2,3-dihalophenols: application to the preparation of indole inhibitors of phospholipase A2
An efficient and regioselective synthesis of 4- and 7-alkoxyindoles has been developed from commercially available starting materials such as 3-halophenols and 3-chloroanisole. Directed ortho-metalation followed by two palladium-catalyzed processes, a Sonogashira coupling and a tandem amination/cyclization reaction, allows the synthesis of regiochemically pure 4- and 7-substituted indoles. This strategy has been successfully applied to the preparation of 2-[3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1H-indol-4-yloxy]acetic acid (LY315920), a known inhibitor of phospholipase A(2).


Accession: 055445848

PMID: 17559277

DOI: 10.1021/jo070643y



Related references

Regioselective synthesis of 4-and 7-alkoxyindoles from 2,3-dihalophenols: Application to the preparation of indole inhibitors of phospholipase A(2). Journal of Organic Chemistry 72(14): 5113-5118, 2007

Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles. Organic & Biomolecular Chemistry 9(14): 5021-5023, 2011

Regioselective Synthesis of Mixed Indole 2,3-Bis(sulfides). A Study of the Mechanism of the Second Sulfenylation of Indole. Journal of Organic Chemistry 61(5): 1573-1577, 1996

Photo induced molecular transformations part 123. one step synthesis of 1h benz f indole 4 9 diones by a new regioselective photoaddition of 2 amino 1 4 naphthoquinone with various alkenes and its application to one step synthesis of kinamycin skeleton. Helvetica Chimica Acta 74(5): 1091-1094, 1991

Synthesis and structure activity relationships of indole Cytosolic Phospholipase A2alpha inhibitors Optimization of the pharmacophore. Abstracts of Papers American Chemical Society 224(1-2): MEDI 319, 2002

Indole inhibitors of human nonpancreatic secretory phospholipase A2. 3. Indole-3-glyoxamides. Journal of Medicinal Chemistry 39(26): 5159-5175, 1996

Indole inhibitors of human nonpancreatic secretory phospholipase A2. 1. Indole-3-acetamides. Journal of Medicinal Chemistry 39(26): 5119-5136, 1996

Indole inhibitors of human nonpancreatic secretory phospholipase A2. 2. Indole-3-acetamides with additional functionality. Journal of Medicinal Chemistry 39(26): 5137-5158, 1996

Design, synthesis, and biological evaluation of 3-(1-Aryl-1H-indol-5-yl)propanoic acids as new indole-based cytosolic phospholipase A2α inhibitors. Journal of Medicinal Chemistry 57(17): 7244-7262, 2014

Synthesis of triphenylarsonium methylide, a new 11C-precursor Application in the preparation of indole. Journal of Labelled Compounds & Radiopharmaceuticals 42(8): 725-736, Aug, 1999