Literature DB >> 20131765

Domino Heck-aza-Michael reactions: efficient access to 1-substituted tetrahydro-beta-carbolines.

Daniel L Priebbenow1, Luke C Henderson, Frederick M Pfeffer, Scott G Stewart.   

Abstract

A simple and efficient palladium-catalyzed domino reaction for the synthesis of a series of C1-substituted tetrahydro-beta-carbolines is described. This domino process involves a Heck reaction at the indole 2-position of a halogenated tryptamine precursor, followed by intramolecular aza-Michael addition.

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Year:  2010        PMID: 20131765     DOI: 10.1021/jo902652h

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

Authors:  Qin Zang; Salim Javed; Patrick Porubsky; Farman Ullah; Benjamin Neuenswander; Gerald H Lushington; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-02-06       Impact factor: 3.784

2.  Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.

Authors:  Qin Zang; Aihua Zhou; Salim Javed; Pradip K Maity; Chris A Knudtson; Danse Bi; Jared J Hastings; Fatima Z Basha; Paul R Hanson
Journal:  Heterocycles       Date:  2012-12-31       Impact factor: 0.831

3.  Synthesis of the pentacyclic skeleton of the indole alkaloid arboflorine.

Authors:  Raul A Leal; Danial R Beaudry; Saeed K Alzghari; Richmond Sarpong
Journal:  Org Lett       Date:  2012-09-28       Impact factor: 6.005

4.  Triazole-containing isothiazolidine 1,1-dioxide library synthesis: one-pot, multi-component protocols for small molecular probe discovery.

Authors:  Alan Rolfe; Thomas O Painter; Naeem Asad; Moon Young Hur; Kyu Ok Jeon; Marek Brzozowski; Sarra V Klimberg; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-08-25       Impact factor: 3.784

5.  Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

Authors:  Qin Zang; Salim Javed; Farman Ullah; Aihua Zhou; Christopher A Knudtson; Danse Bi; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  Synthesis (Stuttg)       Date:  2011-09-01       Impact factor: 3.157

6.  Synthesis and structure-activity relationship of mono-indole-, bis-indole-, and tris-indole-based sulfonamides as potential anticancer agents.

Authors:  Ratchanok Pingaew; Supaluk Prachayasittikul; Somsak Ruchirawat; Virapong Prachayasittikul
Journal:  Mol Divers       Date:  2013-06-28       Impact factor: 2.943

  6 in total

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