Literature DB >> 19035838

Application of ynamides in the synthesis of 2-amidoindoles.

Karin Dooleweerdt1, Thomas Ruhland, Troels Skrydstrup.   

Abstract

A Pd-catalyzed, one-pot, two-step synthesis of 2-amidoindoles from ynamides and o-iodoanilines is reported. A key highlight of this sequence is that after the Sonogashira reaction, intramolecular cyclization to the indole occurs spontaneously without activation of the alkyne.

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Year:  2009        PMID： 19035838     DOI： 10.1021/ol802477d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

4.  A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

Authors:  Hongyan Li; Jennifer E Antoline; Jin-Haek Yang; Ziyad F Al-Rashid; Richard P Hsung
Journal:  New J Chem       Date:  2010-01-01       Impact factor: 3.591

5.  Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Chem Commun (Camb)       Date:  2014-02-12       Impact factor: 6.222

6.  Highly substituted 2-amido-furans from Rh(II)-catalyzed cyclopropenations of ynamides.

Authors:  Hongyan Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

7.  Synthesis of amidines using N-allyl ynamides. A palladium-catalyzed allyl transfer through an ynamido-pi-allyl complex.

Authors:  Yu Zhang; Kyle A DeKorver; Andrew G Lohse; Yan-Shi Zhang; Jian Huang; Richard P Hsung
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

8.  A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

Authors:  Jossian Oppenheimer; Whitney L Johnson; Ruth Figueroa; Ryuji Hayashi; Richard P Hsung
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

9.  Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Authors:  Peng Zhang; Andrea M Cook; Yang Liu; Christian Wolf
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354

10.  1,2-N-migration in a gold-catalysed synthesis of functionalised indenes by the 1,1-carboalkoxylation of ynamides.

Authors:  Holly V Adcock; Thomas Langer; Paul W Davies
Journal:  Chemistry       Date:  2014-05-14       Impact factor: 5.236
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