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

Marta Camarasa; Christian Barnils; Raimon Puig De La Bellacasa; Jordi Teixidó; José I. Borrell

doi:10.1007/s11030-013-9450-1

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

Marta Camarasa, Christian Barnils, Raimon Puig De La Bellacasa, Jordi Teixidó, José I. Borrell^*

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

11 Citations (Scopus)

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{x} (G = NH ₂) and 20{x } (G = SMe) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{x}) with the corresponding 6-aminopyrimidin-4(3H) -one (13 (G=NH₂)); 19 (G =SMe)) in presence of a base under microwave irradiation. The resulting pyrido[2,3-d ]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.

Original language	English
Pages (from-to)	525-536
Number of pages	12
Journal	Molecular Diversity
Volume	17
Issue number	3
DOIs	https://doi.org/10.1007/s11030-013-9450-1
Publication status	Published - Aug 2013

Keywords

2-Aryl acrylates
4-Oxopyrido[2,3-d ]pyrimidines
6-Aminopyrimidine-4 (3H) -ones
Michael addition
Pyrido[2,3-d ]pyrimidines

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

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{x} (G = NH 2) and 20{x } (G = SMe) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{x}) with the corresponding 6-aminopyrimidin-4(3H) -one (13 (G=NH2)); 19 (G =SMe)) in presence of a base under microwave irradiation. The resulting pyrido[2,3-d ]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.",

keywords = "2-Aryl acrylates, 4-Oxopyrido[2,3-d ]pyrimidines, 6-Aminopyrimidine-4 (3H) -ones, Michael addition, Pyrido[2,3-d ]pyrimidines",

author = "Marta Camarasa and Christian Barnils and {Puig De La Bellacasa}, Raimon and Jordi Teixid{\'o} and Borrell, {Jos{\'e} I.}",

note = "Funding Information: Acknowledgments Financial support by the Spanish Ministerio de Economia y Competividad Project SAF2010-C21617-C02 is greatly acknowledged. M. Camarasa wants to thank IQS for a scholarship.",

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language = "English",

volume = "17",

pages = "525--536",

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AU - Camarasa, Marta

AU - Barnils, Christian

AU - Puig De La Bellacasa, Raimon

AU - Teixidó, Jordi

AU - Borrell, José I.

N1 - Funding Information: Acknowledgments Financial support by the Spanish Ministerio de Economia y Competividad Project SAF2010-C21617-C02 is greatly acknowledged. M. Camarasa wants to thank IQS for a scholarship.

PY - 2013/8

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N2 - 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{x} (G = NH 2) and 20{x } (G = SMe) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{x}) with the corresponding 6-aminopyrimidin-4(3H) -one (13 (G=NH2)); 19 (G =SMe)) in presence of a base under microwave irradiation. The resulting pyrido[2,3-d ]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.

AB - 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{x} (G = NH 2) and 20{x } (G = SMe) is described. This methodology is based on reacting a 2-aryl-substituted acrylate (16{x}) with the corresponding 6-aminopyrimidin-4(3H) -one (13 (G=NH2)); 19 (G =SMe)) in presence of a base under microwave irradiation. The resulting pyrido[2,3-d ]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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KW - Michael addition

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ER -

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

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Keywords

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