Literature DB >> 29398786

A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines.

Jill B Williamson1, Emily R Smith1, Jonathan R Scheerer1.   

Abstract

A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels-Alder, and retrograde Diels-Alder with loss of CO2 occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.

Entities:  

Keywords:  Alder; Diels; cycloaddition; cycloreversion; domino reactions; oxazinone; pyridine synthesis

Year:  2017        PMID： 29398786      PMCID： PMC5791744          DOI： 10.1055/s-0036-1588729

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  15 in total

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Authors:  Lutz F. Tietze
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.

Authors:  Jesús A Varela; Carlos Saá
Journal:  Chem Rev       Date:  2003-09       Impact factor: 60.622

Review 3.  Synthesis of pyridine and dihydropyridine derivatives by regio- and stereoselective addition to N-activated pyridines.

Authors:  James A Bull; James J Mousseau; Guillaume Pelletier; André B Charette
Journal:  Chem Rev       Date:  2012-02-21       Impact factor: 60.622

4.  Recent strategies for the synthesis of pyridine derivatives.

Authors:  Matthew D Hill
Journal:  Chemistry       Date:  2010-10-25       Impact factor: 5.236

Review 5.  Quinoline, quinazoline and acridone alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2005-08-24       Impact factor: 13.423

6.  Efficient entry to the [2.2.2]-diazabicyclic ring system via diastereoselective domino reaction sequence.

Authors:  Kaila A Margrey; Alex J Chinn; Stephen W Laws; Robert D Pike; Jonathan R Scheerer
Journal:  Org Lett       Date:  2012-05-09       Impact factor: 6.005

7.  Metal-free cyclotrimerization for the de novo synthesis of pyridines.

Authors:  Karolin Kral; Marko Hapke
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-01       Impact factor: 15.336

8.  Metal-free multicomponent syntheses of pyridines.

Authors:  Christophe Allais; Jean-Marie Grassot; Jean Rodriguez; Thierry Constantieux
Journal:  Chem Rev       Date:  2014-10-10       Impact factor: 60.622

9.  Synthesis of 2-pyridones by cycloreversion of [2.2.2]- bicycloalkene diketopiperazines.

Authors:  Kaila A Margrey; Amy D Hazzard; Jonathan R Scheerer
Journal:  Org Lett       Date:  2014-01-29       Impact factor: 6.005

10.  3,4- and 3,5-Disubstituted 2-Pyridones Using an Intermolecular Cycloaddition / Cycloreversion Strategy: Toward the Synthesis of Aristopyridinone A.

Authors:  Maren K Leibowitz; Ethan S Winter; Jonathan R Scheerer
Journal:  Tetrahedron Lett       Date:  2015-10-28       Impact factor: 2.415
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  1 in total

1.  Synthesis and Spectrophotometric Analysis of 1-Azafluorenone Derivatives.

Authors:  Nicholas H Angello; Robert E Wiley; Christopher J Abelt; Jonathan R Scheerer
Journal:  Molecules       Date:  2020-07-24       Impact factor: 4.411
  1 in total

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