Publicação
Dialkyl imidazolinones from alpha,alpha-dialkyl glycines
| Resumo: | In recent years, our group has been involved in the use of the Ugi-Passerini reaction for the synthesis of several alpha,alpha-dialkylglycines. The C-terminal amide bond of the resulting Ugi adducts 1 proved to be very sensitive to TFA, cleaving readily by a mechanism involving an oxazolinium-type intermediate 2. This intermediate allows in situ functionalization of the C-terminus by reaction with several nucleophiles, affording different derivatives such as free acids, esters and amides. Our previous results suggested that a dipeptide could be obtained if an amino acid ester was used as the nucleophile. The results obtained so far indicate that although a small amount the required dipeptides 3 is formed, 5,5-dialkyl-imidazolin-4-ones 4 are the major products. These may result from competitive attack at the less hindered C-2 of the oxazolinium intermediate, followed by rearrangement. |
|---|---|
| Autores principais: | Costa, Susana P. G. |
| Outros Autores: | Maia, Hernâni L. S.; Lima, Sílvia M. M. A. Pereira |
| Assunto: | Alpha,alpha-dialkyl glycines Dialkyl imidazolinones |
| Ano: | 2003 |
| País: | Portugal |
| Tipo de documento: | outro |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1877774584454840320 |
|---|---|
| author | Costa, Susana P. G. |
| author2 | Maia, Hernâni L. S. Lima, Sílvia M. M. A. Pereira |
| author2_role | author author |
| author_facet | Costa, Susana P. G. Maia, Hernâni L. S. Lima, Sílvia M. M. A. Pereira |
| author_role | author |
| contributor_name_str_mv | RepositóriUM - Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Costa, Susana P. G.\"},{\"Person.name\":\"Maia, Hernâni L. S.\"},{\"Person.name\":\"Lima, Sílvia M. M. A. Pereira\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | RepositóriUM - Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Costa, Susana P. G. Maia, Hernâni L. S. Lima, Sílvia M. M. A. Pereira |
| datacite.date.Accepted.fl_str_mv | 2003-01-01T00:00:00Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Alpha,alpha-dialkyl glycines Dialkyl imidazolinones |
| datacite.titles.title.fl_str_mv | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| dc.contributor.none.fl_str_mv | RepositóriUM - Universidade do Minho |
| dc.creator.none.fl_str_mv | Costa, Susana P. G. Maia, Hernâni L. S. Lima, Sílvia M. M. A. Pereira |
| dc.date.Accepted.fl_str_mv | 2003-01-01T00:00:00Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/1931 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | American Peptide Society |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Alpha,alpha-dialkyl glycines Dialkyl imidazolinones |
| dc.title.fl_str_mv | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_1843 |
| description | In recent years, our group has been involved in the use of the Ugi-Passerini reaction for the synthesis of several alpha,alpha-dialkylglycines. The C-terminal amide bond of the resulting Ugi adducts 1 proved to be very sensitive to TFA, cleaving readily by a mechanism involving an oxazolinium-type intermediate 2. This intermediate allows in situ functionalization of the C-terminus by reaction with several nucleophiles, affording different derivatives such as free acids, esters and amides. Our previous results suggested that a dipeptide could be obtained if an amino acid ester was used as the nucleophile. The results obtained so far indicate that although a small amount the required dipeptides 3 is formed, 5,5-dialkyl-imidazolin-4-ones 4 are the major products. These may result from competitive attack at the less hindered C-2 of the oxazolinium intermediate, followed by rearrangement. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | other |
| id | rum_6fdefc82328aedb81c0abf0038fb8a0f |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/1931 |
| inst_facet_str | urn:organizationAcronym:repositorium{{{_:::_}}}Universidade do Minho |
| 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:1822/1931 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Costa, Susana P. G. Maia, Hernâni L. S. Lima, Sílvia M. M. A. Pereira |
| publishDate | 2003 |
| publisher.none.fl_str_mv | American Peptide Society |
| repo_facet_str | urn:repositoryAcronym:rum{{{_:::_}}}RepositóriUM - Universidade do Minho |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engAmerican Peptide SocietyengIn recent years, our group has been involved in the use of the Ugi-Passerini reaction for the synthesis of several alpha,alpha-dialkylglycines. The C-terminal amide bond of the resulting Ugi adducts 1 proved to be very sensitive to TFA, cleaving readily by a mechanism involving an oxazolinium-type intermediate 2. This intermediate allows in situ functionalization of the C-terminus by reaction with several nucleophiles, affording different derivatives such as free acids, esters and amides. Our previous results suggested that a dipeptide could be obtained if an amino acid ester was used as the nucleophile. The results obtained so far indicate that although a small amount the required dipeptides 3 is formed, 5,5-dialkyl-imidazolin-4-ones 4 are the major products. These may result from competitive attack at the less hindered C-2 of the oxazolinium intermediate, followed by rearrangement.application/pdfengDialkyl imidazolinones from alpha,alpha-dialkyl glycinesCosta, Susana P. G.Maia, Hernâni L. S.Lima, Sílvia M. M. A. PereiraHostingInstitutionOrganizationalRepositóriUM - Universidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISBNIsPartOf0-9715560-1-6ISSNIsPartOf0006-352520032003-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/1931http://purl.org/coar/access_right/c_abf2open accessAlpha,alpha-dialkyl glycinesDialkyl imidazolinones58751 bytesother research producthttp://purl.org/coar/resource_type/c_1843otherhttp://purl.org/coar/access_right/c_abf2application/pdfhttps://repositorium.uminho.pt/bitstreams/1f39f95a-2be1-4591-9c6a-6fd29999d972/download |
| spellingShingle | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines Costa, Susana P. G. Alpha,alpha-dialkyl glycines Dialkyl imidazolinones |
| status | SINGLETON |
| subject.fl_str_mv | Alpha,alpha-dialkyl glycines Dialkyl imidazolinones |
| title | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| title_full | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| title_fullStr | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| title_full_unstemmed | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| title_short | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| title_sort | Dialkyl imidazolinones from alpha,alpha-dialkyl glycines |
| topic | Alpha,alpha-dialkyl glycines Dialkyl imidazolinones |
| topic_facet | Alpha,alpha-dialkyl glycines Dialkyl imidazolinones |
| url | https://hdl.handle.net/1822/1931 |
| visible | 1 |
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