Literature DB >> 21173952

Continuous flow thermolysis of azidoacrylates for the synthesis of heterocycles and pharmaceutical intermediates.

Alexander G O'Brien1, François Lévesque, Peter H Seeberger.   

Abstract

An efficient, safe and scalable procedure for the continuous flow thermolysis of azidoacrylates to yield indoles has been developed and was applied to the synthesis of related heterocycles. The scalability of the process was demonstrated in the continuous flow synthesis of a precursor to the DAAO inhibitor 4H-furo[3,2-b]pyrrole-5-carboxylic acid.

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Year:  2010        PMID: 21173952     DOI: 10.1039/c0cc04481d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  9 in total

1.  Automated Multistep Continuous Flow Synthesis of 2-(1H-Indol-3-yl)thiazole Derivatives.

Authors:  Nicholas Pagano; Marintha L Heil; Nicholas D P Cosford
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

Review 2.  Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis.

Authors:  Bao Hu; Stephen G DiMagno
Journal:  Org Biomol Chem       Date:  2015-04-07       Impact factor: 3.876

3.  Visible-light sensitization of vinyl azides by transition-metal photocatalysis.

Authors:  Elliot P Farney; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-26       Impact factor: 15.336

4.  Continuous flow photolysis of aryl azides: Preparation of 3H-azepinones.

Authors:  Farhan R Bou-Hamdan; François Lévesque; Alexander G O'Brien; Peter H Seeberger
Journal:  Beilstein J Org Chem       Date:  2011-08-17       Impact factor: 2.883

5.  Optimization of chemical functionalities of indole-2-carboxamides to improve allosteric parameters for the cannabinoid receptor 1 (CB1).

Authors:  Leepakshi Khurana; Hamed I Ali; Teresa Olszewska; Kwang H Ahn; Aparna Damaraju; Debra A Kendall; Dai Lu
Journal:  J Med Chem       Date:  2014-03-27       Impact factor: 7.446

Review 6.  Current status and future prospects for enabling chemistry technology in the drug discovery process.

Authors:  Stevan W Djuric; Charles W Hutchins; Nari N Talaty
Journal:  F1000Res       Date:  2016-09-30

Review 7.  Continuous Flow Synthesis of Heterocycles: A Recent Update on the Flow Synthesis of Indoles.

Authors:  Marco Colella; Leonardo Degennaro; Renzo Luisi
Journal:  Molecules       Date:  2020-07-16       Impact factor: 4.411

8.  Synthesis and characterization of S,N-heterotetracenes.

Authors:  Astrid Vogt; Florian Henne; Christoph Wetzel; Elena Mena-Osteritz; Peter Bäuerle
Journal:  Beilstein J Org Chem       Date:  2020-10-26       Impact factor: 2.883

9.  Isomerization of 5-(2H-Azirin-2-yl)oxazoles: An Atom-Economic Approach to 4H-Pyrrolo[2,3-d]oxazoles.

Authors:  Timur O Zanakhov; Ekaterina E Galenko; Mariya A Kryukova; Mikhail S Novikov; Alexander A Khlebnikov
Journal:  Molecules       Date:  2021-03-26       Impact factor: 4.411

  9 in total

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