Literature DB >> 14682774

A powerful new strategy for diversity-oriented synthesis of pyrroles from donor-acceptor cyclopropanes and nitriles.

Ming Yu1, Brian L Pagenkopf.   

Abstract

Lewis acid activated donor-acceptor cyclopropanes react with aliphatic, aromatic, and alpha,beta-unsaturated nitriles in a novel cascade [3 + 2] dipolar cycloaddition, dehydration, and tautomerization sequence to afford pyrroles in moderate to excellent overall yield. This cost-effective and regiospecific method is ideally suited for the preparation of combinatorial libraries. [reaction: see text]

Entities:  

Year:  2003        PMID: 14682774     DOI: 10.1021/ol036180+

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


  5 in total

1.  Functionalized 2,2'-Bipyrroles: Building Blocks for Pyrrolic Macrocycles.

Authors:  Gonzalo Anguera; James T Brewster; David Sánchez-García; Jonathan L Sessler
Journal:  Macroheterocycles       Date:  2018       Impact factor: 1.200

2.  Microwave-assisted Piloty-Robinson synthesis of 3,4-disubstituted pyrroles.

Authors:  Benjamin C Milgram; Katrine Eskildsen; Steven M Richter; W Robert Scheidt; Karl A Scheidt
Journal:  J Org Chem       Date:  2007-04-14       Impact factor: 4.354

3.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

4.  Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes.

Authors:  Amanda Bunyamin; Carol Hua; Anastasios Polyzos; Daniel L Priebbenow
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825

5.  (4+3) Annulation of Donor-Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones.

Authors:  Stefano Nicolai; Jérôme Waser
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-28       Impact factor: 16.823

  5 in total

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