Literature DB >> 17137394

Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction.

Alexei Ilyin1, Volodymyr Kysil, Mikhail Krasavin, Irina Kurashvili, Alexandre V Ivachtchenko.   

Abstract

The unexpected rearrangement of 2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1-one products of the tandem Ugi 4CC/intramolecular Diels-Alder reaction in 85% H3PO4 was discovered to provide diastereomerically pure tricyclic bislactam lactone-containing natural product-like products in high yield. Mechanistic rationale for the observed rearrangement was proposed and has been tentatively confirmed by additional experiments.

Entities:  

Year:  2006        PMID： 17137394     DOI： 10.1021/jo061825f

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


  4 in total

1.  Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade.

Authors:  Steven Gunawan; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2013-08-14       Impact factor: 2.415

2.  Ugi/aldol sequence: expeditious entry to several families of densely substituted nitrogen heterocycles.

Authors:  Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-29       Impact factor: 15.336

3.  Synthesis of terephthalic acid via Diels-Alder reactions with ethylene and oxidized variants of 5-hydroxymethylfurfural.

Authors:  Joshua J Pacheco; Mark E Davis
Journal:  Proc Natl Acad Sci U S A       Date:  2014-05-27       Impact factor: 11.205

4.  Application of heterocyclic aldehydes as components in Ugi-Smiles couplings.

Authors:  Katelynn M Mason; Michael S Meyers; Abbie M Fox; Sarah B Luesse
Journal:  Beilstein J Org Chem       Date:  2016-09-15       Impact factor: 2.883
  4 in total

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