Literature DB >> 18947184

Sustainable synthetic methods: domino construction of dihydropyridin-4-ones and beta-amino esters in aqueous ethanol.

Peter J Alaimo1, Robert O'Brien, Adam W Johnson, Sarah R Slauson, Jeannette M O'Brien, Elizabeth L Tyson, Amanda-Lynn Marshall, Colleen E Ottinger, Jon G Chacon, Lorien Wallace, Corey Y Paulino, Sarah Connell.   

Abstract

Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In(0) generates an amine and In (III) byproducts. Addition of aldehyde followed by Danishefsky's diene or silyl ketene acetal provides access to dihydropyridin-4-ones or beta-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions.

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Year:  2008        PMID: 18947184     DOI: 10.1021/ol801911f

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


  2 in total

1.  Microwave-assisted synthesis of novel 2,3-dihydro-4-pyridinones.

Authors:  Bahjat A Saeed; Rita S Elias; Wisam A Radhi
Journal:  Molecules       Date:  2010-11-17       Impact factor: 4.411

Review 2.  Recent advances in the chemistry of imine-based multicomponent reactions (MCRs).

Authors:  Lokman H Choudhury; Tasneem Parvin
Journal:  Tetrahedron       Date:  2011-07-18       Impact factor: 2.457

  2 in total

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