Literature DB >> 20000451

An unusual Michael addition of 3,3-dimethoxypropanenitrile to 2-aryl acrylates: a convenient route to 4-unsubstituted 5,6-dihydropyrido[2,3-d]pyrimidines.

Xavier Berzosa1, Xavier Bellatriu, Jordi Teixidó, José I Borrell.   

Abstract

An unusual Michael addition between 2-aryl-substituted acrylates and 3,3-dimethoxypropanenitrile which leads, depending on the reaction temperature (60 or -78 degrees C, respectively), to a 4-methoxymethylene-substituted 4-cyanobutyric ester or to a 4-dimethoxymethyl 4-cyanobutyric ester is described. These compounds can be subsequently converted to 4-unsubstituted pyrido[2,3-d]pyrimidines upon treatment with a guanidine system under microwave irradiation.

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Year:  2010        PMID: 20000451     DOI: 10.1021/jo902345r

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


  4 in total

1.  A diversity-oriented synthesis of 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5-yl)propanoic esters.

Authors:  Xavier Berzosa; Sofia Pettersson; Jordi Teixidó; José I Borrell
Journal:  Mol Divers       Date:  2010-11-12       Impact factor: 2.943

2.  Synthesis of 2-arylamino substituted 5,6-dihydropyrido[2,3-d]pyrimidine-7(8H)-ones from arylguanidines.

Authors:  Iñaki Galve; Raimon Puig de la Bellacasa; David Sánchez-García; Xavier Batllori; Jordi Teixidó; José I Borrell
Journal:  Mol Divers       Date:  2012-10-10       Impact factor: 2.943

3.  A new and practical method for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(₃Η,8Η)-diones.

Authors:  Marta Camarasa; Christian Barnils; Raimon Puig de la Bellacasa; Jordi Teixidó; José I Borrell
Journal:  Mol Divers       Date:  2013-05-26       Impact factor: 2.943

Review 4.  Pyrido[2,3-d]pyrimidin-7(8H)-ones: Synthesis and Biomedical Applications.

Authors:  Guillem Jubete; Raimon Puig de la Bellacasa; Roger Estrada-Tejedor; Jordi Teixidó; José I Borrell
Journal:  Molecules       Date:  2019-11-16       Impact factor: 4.411

  4 in total

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