An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones

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Title:An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones
Creators:
Borrell, José I.
Teixidó, Jordi
Martínez-Teipel, Blanca
Serra, Blanca
Matallana, Josep Lluís
Costa, Marta
Batllori, Xavier
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 6, pp. 901-909
Uncontrolled Keywords:2-Oxopyrido[2,3-<i>d</i>]pyrimidines, Michael reaction, Dinitrile cyclization, 4-Oxopyrido[2,3-<i>d</i>]pyrimidines

Abstract

An unequivocal set of procedures for the synthesis of 4-amino-1,5,6,8-tetrahydropyrido[2,3-<i>d</i>]pyrimidine-2,7-diones (<strong>7</strong>) and 2-amino-3,5,6,8-tetrahydropyrido[2,3-<i>d</i>]pyrimidine-4,7-diones (<strong>8</strong>), in a maximum of four steps from an α,β-unsaturated ester <strong>1</strong>, is reported. Thus, the acid hydrolysis of the 2,4-diaminopyrido[2,3-<i>d</i>]pyrimidines <strong>3</strong> yields the 4-amino-2-oxopyrido[2,3-<i>d</i>]pyrimidines <strong>7</strong> while the cyclization of the Michael adducts <strong>9</strong> (formed by reaction of <strong>1</strong> and methyl cyanoacetate) with guanidine affords the corresponding 2-amino-4-oxopyrido[2,3-<i>d</i>]pyrimidines <strong>8</strong>. Both isomers were also obtained by hydrolysis of the 4-amino-2-bromo- and 2-amino-4-bromo-5,6-dihydropyrido[2,3-<i>d</i>]pyrimidin-7(8<i>H</i>)-ones <strong>5</strong> and <strong>6</strong>, respectively.

Title:An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones
Creators:
Borrell, José I.
Teixidó, Jordi
Martínez-Teipel, Blanca
Serra, Blanca
Matallana, Josep Lluís
Costa, Marta
Batllori, Xavier
Uncontrolled Keywords:2-Oxopyrido[2,3-<i>d</i>]pyrimidines, Michael reaction, Dinitrile cyclization, 4-Oxopyrido[2,3-<i>d</i>]pyrimidines
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:6
Page Range:pp. 901-909
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960901UNSPECIFIED
ID Code:991
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Borrell, José I.; Teixidó, Jordi; Martínez-Teipel, Blanca; Serra, Blanca; Matallana, Josep Lluís; Costa, Marta; Batllori, Xavier (1996) An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones. Collection of Czechoslovak Chemical Communications, 61 (6). pp. 901-909. ISSN 0010-0765

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