Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives
A convenient, accessible, and high yield method for preparing of 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1) by treatment of acetoacetic acid ethyl ester with thiourea in sodium methylate was developed. The alkylation of the latter with 3-chloro-pentane-2,4-dione and further regioselective...
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| Format: | Article |
| Language: | English |
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Wiley
2017-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2017/8180913 |
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| author | Vergush A. Pivazyan Emma A. Ghazaryan Roza S. Shainova Rafael A. Tamazyan Armen G. Ayvazyan Aleksandr P. Yengoyan |
| author_facet | Vergush A. Pivazyan Emma A. Ghazaryan Roza S. Shainova Rafael A. Tamazyan Armen G. Ayvazyan Aleksandr P. Yengoyan |
| author_sort | Vergush A. Pivazyan |
| collection | DOAJ |
| description | A convenient, accessible, and high yield method for preparing of 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1) by treatment of acetoacetic acid ethyl ester with thiourea in sodium methylate was developed. The alkylation of the latter with 3-chloro-pentane-2,4-dione and further regioselective cyclization of intermediate compound (2) in high yield afforded 2-acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one (3). The halogenation and some transformations of synthesized thiazolo[3,2-a]pyrimidine (3) due to its ketone group were carried out to obtain the corresponding carboxamide, carbothioamide, sulfonohydrazide, and oxime and its alkylated derivatives (5). At preliminary biological studies the synthesized compounds have shown growth stimulant properties. The activity of four of them was higher than 70%, compared with heteroauxin. |
| format | Article |
| id | doaj-art-e024f4321c1c42a7835336906fc9b65c |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2017-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-e024f4321c1c42a7835336906fc9b65c2025-02-03T06:11:13ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/81809138180913Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one DerivativesVergush A. Pivazyan0Emma A. Ghazaryan1Roza S. Shainova2Rafael A. Tamazyan3Armen G. Ayvazyan4Aleksandr P. Yengoyan5National Agrarian University of Armenia, 74 Teryan Str., 0009 Yerevan, ArmeniaArmenian-Russian (Slavonic) State University, 123 H. Emin Str., 0051 Yerevan, ArmeniaNational Agrarian University of Armenia, 74 Teryan Str., 0009 Yerevan, ArmeniaSTC OPC Molecule Structure Research Center of NAS RA, 26 Azatutyan Av., 0014 Yerevan, ArmeniaSTC OPC Molecule Structure Research Center of NAS RA, 26 Azatutyan Av., 0014 Yerevan, ArmeniaNational Agrarian University of Armenia, 74 Teryan Str., 0009 Yerevan, ArmeniaA convenient, accessible, and high yield method for preparing of 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1) by treatment of acetoacetic acid ethyl ester with thiourea in sodium methylate was developed. The alkylation of the latter with 3-chloro-pentane-2,4-dione and further regioselective cyclization of intermediate compound (2) in high yield afforded 2-acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one (3). The halogenation and some transformations of synthesized thiazolo[3,2-a]pyrimidine (3) due to its ketone group were carried out to obtain the corresponding carboxamide, carbothioamide, sulfonohydrazide, and oxime and its alkylated derivatives (5). At preliminary biological studies the synthesized compounds have shown growth stimulant properties. The activity of four of them was higher than 70%, compared with heteroauxin.http://dx.doi.org/10.1155/2017/8180913 |
| spellingShingle | Vergush A. Pivazyan Emma A. Ghazaryan Roza S. Shainova Rafael A. Tamazyan Armen G. Ayvazyan Aleksandr P. Yengoyan Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives Journal of Chemistry |
| title | Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives |
| title_full | Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives |
| title_fullStr | Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives |
| title_full_unstemmed | Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives |
| title_short | Synthesis and Growth Stimulant Properties of 2-Acetyl-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one Derivatives |
| title_sort | synthesis and growth stimulant properties of 2 acetyl 3 7 dimethyl 5h thiazolo 3 2 a pyrimidin 5 one derivatives |
| url | http://dx.doi.org/10.1155/2017/8180913 |
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