Literature DB >> 23709350

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

Marta Camarasa1, Christian Barnils, Raimon Puig de la Bellacasa, Jordi Teixidó, José I Borrell.   

Abstract

A one step general synthetic methodology for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-diones (17{[Formula: see text]} ([Formula: see text]) and 20{[Formula: see text]} ([Formula: see text])) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{[Formula: see text]}) with the corresponding 6-aminopyrimidin-4(3[Formula: see text]-one (13 ([Formula: see text]; 19 ([Formula: see text])) in presence of a base under microwave irradiation. The resulting pyrido[2,3-[Formula: see text]]pyrimidines present an aryl substituent at position C6, precisely the one directly related to the biological activity of such heterocycles. These protocols have been extended to other 2-alkyl-substituted and 3-alkyl (or aryl)-substituted acrylates but with lower yields.

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Year:  2013        PMID： 23709350     DOI： 10.1007/s11030-013-9450-1

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  10 in total

1.  New potential inhibitors of cyclin-dependent kinase 4: design and synthesis of pyrido[2,3-d]pyrimidine derivatives under microwave irradiation.

Authors:  Shujiang Tu; Jinpeng Zhang; Xiaotong Zhu; Jianing Xu; Yan Zhang; Qian Wang; Runhong Jia; Bo Jiang; Junyong Zhang
Journal:  Bioorg Med Chem Lett       Date:  2006-04-18       Impact factor: 2.823

2.  Derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine as novel, potent, and selective A3 adenosine receptor antagonists.

Authors:  Barbara Cosimelli; Giovanni Greco; Marina Ehlardo; Ettore Novellino; Federico Da Settimo; Sabrina Taliani; Concettina La Motta; Marusca Bellandi; Tiziano Tuccinardi; Adriano Martinelli; Osele Ciampi; Maria Letizia Trincavelli; Claudia Martini
Journal:  J Med Chem       Date:  2008-02-13       Impact factor: 7.446

3.  An efficient direct amination of cyclic amides and cyclic ureas.

Authors:  Zhao-Kui Wan; Sumrit Wacharasindhu; Eva Binnun; Tarek Mansour
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

4.  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.

Authors:  Xavier Berzosa; Xavier Bellatriu; Jordi Teixidó; José I Borrell
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

5.  2-Substituted aminopyrido[2,3-d]pyrimidin-7(8H)-ones. structure-activity relationships against selected tyrosine kinases and in vitro and in vivo anticancer activity.

Authors:  S R Klutchko; J M Hamby; D H Boschelli; Z Wu; A J Kraker; A M Amar; B G Hartl; C Shen; W D Klohs; R W Steinkampf; D L Driscoll; J M Nelson; W L Elliott; B J Roberts; C L Stoner; P W Vincent; D J Dykes; R L Panek; G H Lu; T C Major; T K Dahring; H Hallak; L A Bradford; H D Showalter; A M Doherty
Journal:  J Med Chem       Date:  1998-08-13       Impact factor: 7.446

6.  Multisubstituted quinoxalines and pyrido[2,3-d]pyrimidines: synthesis and SAR study as tyrosine kinase c-Met inhibitors.

Authors:  Kui Wu; Jing Ai; Qiufeng Liu; TianTian Chen; Ailing Zhao; Xia Peng; Yuanxiang Wang; Yinchun Ji; Qizheng Yao; Yechun Xu; Meiyu Geng; Ao Zhang
Journal:  Bioorg Med Chem Lett       Date:  2012-08-27       Impact factor: 2.823

7.  A one-pot microwave-assisted synthesis of pyrido[2,3-d]pyrimidines.

Authors:  Núria Mont; Jordi Teixidó; C Oliver Kappe; José I Borrell
Journal:  Mol Divers       Date:  2003       Impact factor: 2.943

8.  A diversity oriented, microwave assisted synthesis of N-substituted 2-hydro-4-amino-pyrido[2,3-d]pyrimidin-7(8H)-ones.

Authors:  Núria Mont; Jordi Teixidó; José I Borrell
Journal:  Mol Divers       Date:  2008-11-27       Impact factor: 2.943

9.  A simple method for C-6 modification of guanine nucleosides.

Authors:  Mahesh K Lakshman; Josh Frank
Journal:  Org Biomol Chem       Date:  2009-06-01       Impact factor: 3.876

10.  Palladium-catalyzed cross-coupling of alpha-diazocarbonyl compounds with arylboronic acids.

Authors:  Cheng Peng; Yan Wang; Jianbo Wang
Journal:  J Am Chem Soc       Date:  2008-01-11       Impact factor: 15.419
  10 in total
  2 in total

1.  Merging catalyst-free synthesis and iodine catalysis: one-pot synthesis of dihydrofuropyrimidines and spirodihydrofuropyrimidine pyrazolones.

Authors:  Ya-Yun Zheng; Kai-Xiang Feng; Ai-Bao Xia; Jie Liu; Cheng-Ke Tang; Zhan-Yu Zhou; Dan-Qian Xu
Journal:  RSC Adv       Date:  2019-03-27       Impact factor: 3.361

Review 2.  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
  2 in total

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