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Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts
We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N -azolyl- and С -pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and f...
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| Published in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2015-05, Vol.51 (5), p.483-490 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c425t-a1349259c6465fefc53024c5b2302c044217ce746f2bc140d67c9890b8284e1c3 |
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| cites | cdi_FETCH-LOGICAL-c425t-a1349259c6465fefc53024c5b2302c044217ce746f2bc140d67c9890b8284e1c3 |
| container_end_page | 490 |
| container_issue | 5 |
| container_start_page | 483 |
| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 51 |
| creator | Danagulyan, Gevorg G. Tumanyan, Araksya K. Attaryan, Oganes S. Tamazyan, Rafael A. Danagulyan, Anna G. Ayvazyan, Armen G. |
| description | We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of
N
-azolyl- and
С
-pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-
a
]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-
a
]pyrimidine. |
| doi_str_mv | 10.1007/s10593-015-1724-3 |
| format | article |
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N
-azolyl- and
С
-pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-
a
]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-
a
]pyrimidine.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-015-1724-3</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Chemistry ; Chemistry and Materials Science ; Esters ; Organic acids ; Organic Chemistry ; Pharmacy ; Pyrimidines</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2015-05, Vol.51 (5), p.483-490</ispartof><rights>Springer Science+Business Media New York 2015</rights><rights>COPYRIGHT 2015 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c425t-a1349259c6465fefc53024c5b2302c044217ce746f2bc140d67c9890b8284e1c3</citedby><cites>FETCH-LOGICAL-c425t-a1349259c6465fefc53024c5b2302c044217ce746f2bc140d67c9890b8284e1c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27907,27908</link.rule.ids></links><search><creatorcontrib>Danagulyan, Gevorg G.</creatorcontrib><creatorcontrib>Tumanyan, Araksya K.</creatorcontrib><creatorcontrib>Attaryan, Oganes S.</creatorcontrib><creatorcontrib>Tamazyan, Rafael A.</creatorcontrib><creatorcontrib>Danagulyan, Anna G.</creatorcontrib><creatorcontrib>Ayvazyan, Armen G.</creatorcontrib><title>Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of
N
-azolyl- and
С
-pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-
a
]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-
a
]pyrimidine.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Esters</subject><subject>Organic acids</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Pyrimidines</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kU1LxDAQhoMouK7-AG8Br2bNZ9Mel8UvWPSgnkRCmqZrljZZmu6h--tNqQiCyByGmXmfF4YXgEuCFwRjeRMJFgVDmAhEJOWIHYEZEZKhnAl2DGYY4wIxQukpOItxm0ZJcj4D25fB9582ughDDZ8Q1L6CK6QPoRkaFPdl7F2_720Fd0M3bsM7uRZIf6TRta5y3kZYDrCzZjCNO-jeBT9a_dzdvoVRN308Bye1bqK9-O5z8HZ3-7p6QOvn-8fVco0Mp6JHmjBeUFGYjGeitrURDFNuRElTN5hzSqSxkmc1LQ3huMqkKfIClznNuSWGzcHV5LvRjVXO16HvtGldNGrJJc64yAqWVIs_VKkq2zoTvK1d2v8CyASYLsTY2Vrt0oe6GxTBasxATRmolIEaM1AjQycmJq3f2E5tw77z6ft_oC_Mjoj5</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Danagulyan, Gevorg G.</creator><creator>Tumanyan, Araksya K.</creator><creator>Attaryan, Oganes S.</creator><creator>Tamazyan, Rafael A.</creator><creator>Danagulyan, Anna G.</creator><creator>Ayvazyan, Armen G.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150501</creationdate><title>Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts</title><author>Danagulyan, Gevorg G. ; Tumanyan, Araksya K. ; Attaryan, Oganes S. ; Tamazyan, Rafael A. ; Danagulyan, Anna G. ; Ayvazyan, Armen G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c425t-a1349259c6465fefc53024c5b2302c044217ce746f2bc140d67c9890b8284e1c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Esters</topic><topic>Organic acids</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Pyrimidines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Danagulyan, Gevorg G.</creatorcontrib><creatorcontrib>Tumanyan, Araksya K.</creatorcontrib><creatorcontrib>Attaryan, Oganes S.</creatorcontrib><creatorcontrib>Tamazyan, Rafael A.</creatorcontrib><creatorcontrib>Danagulyan, Anna G.</creatorcontrib><creatorcontrib>Ayvazyan, Armen G.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Danagulyan, Gevorg G.</au><au>Tumanyan, Araksya K.</au><au>Attaryan, Oganes S.</au><au>Tamazyan, Rafael A.</au><au>Danagulyan, Anna G.</au><au>Ayvazyan, Armen G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2015-05-01</date><risdate>2015</risdate><volume>51</volume><issue>5</issue><spage>483</spage><epage>490</epage><pages>483-490</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of
N
-azolyl- and
С
-pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-
a
]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-
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| fulltext | fulltext |
| identifier | ISSN: 0009-3122 |
| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2015-05, Vol.51 (5), p.483-490 |
| issn | 0009-3122 1573-8353 |
| language | eng |
| recordid | cdi_gale_infotracmisc_A470645693 |
| source | Springer Nature |
| subjects | Chemistry Chemistry and Materials Science Esters Organic acids Organic Chemistry Pharmacy Pyrimidines |
| title | Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts |
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