A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation
[Display omitted] A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner...
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| Veröffentlicht in: | Tetrahedron letters 2015-01, Vol.56 (3), p.521-524 |
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| creator | Lim, Felicia Phei Lin Luna, Giuseppe Dolzhenko, Anton V. |
| description | [Display omitted]
A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes. |
| doi_str_mv | 10.1016/j.tetlet.2014.12.010 |
| format | Article |
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A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2014.12.010</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Chemical reactions ; Cyanamides ; Filtration ; Libraries ; Microwave-assisted synthesis ; Microwaves ; Multicomponent reaction ; Organic chemistry ; Purine isostere ; Purity ; Pyrazole ; Tetrahedrons ; Triazine</subject><ispartof>Tetrahedron letters, 2015-01, Vol.56 (3), p.521-524</ispartof><rights>2014 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-d926eac92fcc700b8796a201710f446c587627544420e5600da3994869ae75ce3</citedby><cites>FETCH-LOGICAL-c385t-d926eac92fcc700b8796a201710f446c587627544420e5600da3994869ae75ce3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403914020644$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Lim, Felicia Phei Lin</creatorcontrib><creatorcontrib>Luna, Giuseppe</creatorcontrib><creatorcontrib>Dolzhenko, Anton V.</creatorcontrib><title>A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation</title><title>Tetrahedron letters</title><description>[Display omitted]
A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes.</description><subject>Chemical reactions</subject><subject>Cyanamides</subject><subject>Filtration</subject><subject>Libraries</subject><subject>Microwave-assisted synthesis</subject><subject>Microwaves</subject><subject>Multicomponent reaction</subject><subject>Organic chemistry</subject><subject>Purine isostere</subject><subject>Purity</subject><subject>Pyrazole</subject><subject>Tetrahedrons</subject><subject>Triazine</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kMtOwzAQRS0EEuXxByyyZIHDOHHsZINUIV5SJTawtlxnKlwldrDdIvh63JY1sxlpZu7R3EvIFYOSARO36zJhGjCVFTBesqoEBkdkxlpZ07pp2TGZAXCgHOrulJzFuIZcooUZSfPCO6STTzdF-giI1PhxyiOXCj1a51Ow-sc6LLRzm0En611WJF80dL-fvoP-8QNSTo0OS-9sVgwYi43rMRSjNcF_6S0WNgTd2z3ggpys9BDx8q-fk_fHh7f7Z7p4fXq5ny-oqdsm0b6rBGrTVStjJMCylZ3Q2aJksOJcmKaVopIN57wCbARAr-uu463oNMrGYH1Org_cKfjPDcakRhsNDoN26DdRMZkxUgpo8yk_nOZ3Ywy4UlOwow7fioHahazW6hCy2oWsWKVyyFl2d5BhtrG1GFQ0Fp3B3gY0SfXe_g_4BUYMiSw</recordid><startdate>20150114</startdate><enddate>20150114</enddate><creator>Lim, Felicia Phei Lin</creator><creator>Luna, Giuseppe</creator><creator>Dolzhenko, Anton V.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150114</creationdate><title>A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation</title><author>Lim, Felicia Phei Lin ; Luna, Giuseppe ; Dolzhenko, Anton V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-d926eac92fcc700b8796a201710f446c587627544420e5600da3994869ae75ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Chemical reactions</topic><topic>Cyanamides</topic><topic>Filtration</topic><topic>Libraries</topic><topic>Microwave-assisted synthesis</topic><topic>Microwaves</topic><topic>Multicomponent reaction</topic><topic>Organic chemistry</topic><topic>Purine isostere</topic><topic>Purity</topic><topic>Pyrazole</topic><topic>Tetrahedrons</topic><topic>Triazine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lim, Felicia Phei Lin</creatorcontrib><creatorcontrib>Luna, Giuseppe</creatorcontrib><creatorcontrib>Dolzhenko, Anton V.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lim, Felicia Phei Lin</au><au>Luna, Giuseppe</au><au>Dolzhenko, Anton V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation</atitle><jtitle>Tetrahedron letters</jtitle><date>2015-01-14</date><risdate>2015</risdate><volume>56</volume><issue>3</issue><spage>521</spage><epage>524</epage><pages>521-524</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2014.12.010</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Tetrahedron letters, 2015-01, Vol.56 (3), p.521-524 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Chemical reactions Cyanamides Filtration Libraries Microwave-assisted synthesis Microwaves Multicomponent reaction Organic chemistry Purine isostere Purity Pyrazole Tetrahedrons Triazine |
| title | A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation |
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