Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones

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Title:Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones
Creators:
Toplak, Renata
Svete, Jurij
Golič Grdadolnik, Simona
Stanovnik, Branko
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 2, pp. 177-189
Uncontrolled Keywords:Fused heterocycles, 1,2,4-Triazolo[2,3-<i>a</i>]pyrimidines, Pyrido[1,2-<i>a</i>]pyrimidines, Pyrimido[1,2-<i>b</i>]pyridazines, Pyrazino[1,2-<i>a</i>]pyrimidines, Thiazolo[3,2-<i>a</i>]pyrimidines

Abstract

Methyl (<i>Z</i>)-2-[(benzyloxycarbonyl)amino]-3-dimethylaminopropenoate (<strong>1</strong>) was used as a reagent for preparation of 3-[(benzyloxycarbonyl)amino] substituted 4<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidin-4-ones <strong>17</strong>-<strong>21</strong>, 4<i>H</i>-pyrimido[1,2-<i>b</i>]pyridazin-4-ones <strong>22</strong> and <strong>23</strong>, 5<i>H</i>-[1,2,4]triazolo[2,3-<i>a</i>]- pyrimidin-5-one <strong>24</strong>, 5<i>H</i>-thiazolo[3,2-<i>a</i>]pyrimidin-5-one <strong>25</strong>, and 4<i>H</i>-pyrazino[1,2-<i>a</i>]pyrimidin-4-one <strong>26</strong>. Removal of the benzyloxycarbonyl group by catalytical transfer hydrogenation with Pd/C in the presence of cyclohexene is selective to give 3-amino-4<i>H</i>-pyrido[1,2-<i>a</i>]- pyrimidin-4-ones <strong>27</strong>-<strong>30</strong> in 85-92% yields, or with hydrogen bromide in acetic acid to give 3-amino-4<i>H</i>-pyrimido[1,2-<i>b</i>]pyridazin-4-one (<strong>31</strong>) and 6-amino-5<i>H</i>-thiazolo[3,2-<i>a</i>]pyrimidin-5-one (<strong>32</strong>) in 80% yields.

Title:Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones
Creators:
Toplak, Renata
Svete, Jurij
Golič Grdadolnik, Simona
Stanovnik, Branko
Uncontrolled Keywords:Fused heterocycles, 1,2,4-Triazolo[2,3-<i>a</i>]pyrimidines, Pyrido[1,2-<i>a</i>]pyrimidines, Pyrimido[1,2-<i>b</i>]pyridazines, Pyrazino[1,2-<i>a</i>]pyrimidines, Thiazolo[3,2-<i>a</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:64
Number:2
Page Range:pp. 177-189
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990177UNSPECIFIED
ID Code:1468
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Toplak, Renata; Svete, Jurij; Golič Grdadolnik, Simona; Stanovnik, Branko (1999) Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones. Collection of Czechoslovak Chemical Communications, 64 (2). pp. 177-189. ISSN 0010-0765

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