Publication
A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives
| Summary: | Pyrimido[5,4-d]pyrimidines are biologically important compounds with diverse activity depending on the substituent groups around the heterocycle. The 3,4-dihydropyrimido[5,4-d]pyrimidines are efficiently converted to the aromatic derivatives by Dimroth rearrangement promoted by reaction with piperidine, in a very slow process. Subsequently, the aromatic derivatives are converted to new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives by reaction with aldehydes in an acidic medium. The 4,8-disubstituted-pyrimido[5,4-d]pyrimidines are also obtained much more efficiently by a tandem reaction between the 3,4-dihydropyrimido[5,4-d]pyrimidines, piperidine and a variety of aldehydes. The cascade reaction approach has a broad application since phenyl, haloaryl, alkoxy-aryl, hydroxy-aryl, and heteroaryl aldehydes are compatible with the reaction conditions. The reactions were studied by 1H NMR. These studies support the reaction mechanisms proposals. The tandem approach involves the formation of ionic reactive intermediates that allows explain this approach's efficiency. |
|---|---|
| Main Authors: | Rocha, Ashly |
| Other Authors: | Lopes, André; Teixeira, Sofia; Carvalho, M. Alice |
| Subject: | Dimroth rearrangement Organic catalysis Pyrimidine derivatives Pyrimido[5,4-d]pyrimidines Tandem approach |
| Year: | 2023 |
| Country: | Portugal |
| Document type: | article |
| Access type: | restricted access |
| Associated institution: | Universidade do Minho |
| Language: | English |
| Origin: | RepositóriUM - Universidade do Minho |
| _version_ | 1866877930238377984 |
|---|---|
| author | Rocha, Ashly |
| author2 | Lopes, André Teixeira, Sofia Carvalho, M. Alice |
| author2_role | author author author |
| author_facet | Rocha, Ashly Lopes, André Teixeira, Sofia Carvalho, M. Alice |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Rocha, Ashly\"},{\"Person.name\":\"Lopes, André\"},{\"Person.name\":\"Teixeira, Sofia\"},{\"Person.name\":\"Carvalho, M. Alice\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Rocha, Ashly Lopes, André Teixeira, Sofia Carvalho, M. Alice |
| datacite.date.Accepted.fl_str_mv | 2023-01-01T00:00:00Z |
| datacite.date.embargoed.fl_str_mv | 10000-01-01T00:00:00Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| datacite.subjects.subject.fl_str_mv | Dimroth rearrangement Organic catalysis Pyrimidine derivatives Pyrimido[5,4-d]pyrimidines Tandem approach |
| datacite.titles.title.fl_str_mv | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Rocha, Ashly Lopes, André Teixeira, Sofia Carvalho, M. Alice |
| dc.date.Accepted.fl_str_mv | 2023-01-01T00:00:00Z |
| dc.date.embargoed.fl_str_mv | 10000-01-01T00:00:00Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/87031 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Wiley |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| dc.subject.none.fl_str_mv | Dimroth rearrangement Organic catalysis Pyrimidine derivatives Pyrimido[5,4-d]pyrimidines Tandem approach |
| dc.title.fl_str_mv | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Pyrimido[5,4-d]pyrimidines are biologically important compounds with diverse activity depending on the substituent groups around the heterocycle. The 3,4-dihydropyrimido[5,4-d]pyrimidines are efficiently converted to the aromatic derivatives by Dimroth rearrangement promoted by reaction with piperidine, in a very slow process. Subsequently, the aromatic derivatives are converted to new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives by reaction with aldehydes in an acidic medium. The 4,8-disubstituted-pyrimido[5,4-d]pyrimidines are also obtained much more efficiently by a tandem reaction between the 3,4-dihydropyrimido[5,4-d]pyrimidines, piperidine and a variety of aldehydes. The cascade reaction approach has a broad application since phenyl, haloaryl, alkoxy-aryl, hydroxy-aryl, and heteroaryl aldehydes are compatible with the reaction conditions. The reactions were studied by 1H NMR. These studies support the reaction mechanisms proposals. The tandem approach involves the formation of ionic reactive intermediates that allows explain this approach's efficiency. |
| dirty | 0 |
| eu_rights_str_mv | restrictedAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/8979a2b2-ad96-4b3e-b414-39fb32a1024f/download |
| id | rum_fe01a5bf9f3f972a3545a9847c8f4e68 |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/87031 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/87031 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Rocha, Ashly Lopes, André Teixeira, Sofia Carvalho, M. Alice |
| publishDate | 2023 |
| publisher.none.fl_str_mv | Wiley |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engWileyporPyrimido[5,4-d]pyrimidines are biologically important compounds with diverse activity depending on the substituent groups around the heterocycle. The 3,4-dihydropyrimido[5,4-d]pyrimidines are efficiently converted to the aromatic derivatives by Dimroth rearrangement promoted by reaction with piperidine, in a very slow process. Subsequently, the aromatic derivatives are converted to new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives by reaction with aldehydes in an acidic medium. The 4,8-disubstituted-pyrimido[5,4-d]pyrimidines are also obtained much more efficiently by a tandem reaction between the 3,4-dihydropyrimido[5,4-d]pyrimidines, piperidine and a variety of aldehydes. The cascade reaction approach has a broad application since phenyl, haloaryl, alkoxy-aryl, hydroxy-aryl, and heteroaryl aldehydes are compatible with the reaction conditions. The reactions were studied by 1H NMR. These studies support the reaction mechanisms proposals. The tandem approach involves the formation of ionic reactive intermediates that allows explain this approach's efficiency.application/pdfporA tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivativesRocha, AshlyLopes, AndréTeixeira, SofiaCarvalho, M. AliceHostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf2193-5807DOIIsPartOf10.1002/ajoc.2023002512023-012023-10-20T17:13:08Z2023-01-01T00:00:00Z10000-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/87031http://purl.org/coar/access_right/c_16ecrestricted accessDimroth rearrangementOrganic catalysisPyrimidine derivativesPyrimido[5,4-d]pyrimidinesTandem approach3102548 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_f1cfapplication/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/8979a2b2-ad96-4b3e-b414-39fb32a1024f/download |
| spellingShingle | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives Rocha, Ashly Dimroth rearrangement Organic catalysis Pyrimidine derivatives Pyrimido[5,4-d]pyrimidines Tandem approach |
| status | SINGLETON |
| subject.fl_str_mv | Dimroth rearrangement Organic catalysis Pyrimidine derivatives Pyrimido[5,4-d]pyrimidines Tandem approach |
| title | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| title_full | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| title_fullStr | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| title_full_unstemmed | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| title_short | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| title_sort | A tandem reaction in the synthesis of new 4,8-disubstituted-pyrimido[5,4-d]pyrimidine derivatives |
| topic | Dimroth rearrangement Organic catalysis Pyrimidine derivatives Pyrimido[5,4-d]pyrimidines Tandem approach |
| topic_facet | Dimroth rearrangement Organic catalysis Pyrimidine derivatives Pyrimido[5,4-d]pyrimidines Tandem approach |
| url | https://hdl.handle.net/1822/87031 |
| visible | 1 |