Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2014 |
| Outros Autores: | , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/10061 |
Resumo: | Indian Institute of Technology Bombay. Department of Chemistry. Mombai, India. |
| id |
CRUZ_c1d64d36caac9de2f44a4cb3715e5a7b |
|---|---|
| oai_identifier_str |
oai:www.arca.fiocruz.br:icict/10061 |
| network_acronym_str |
CRUZ |
| network_name_str |
Repositório Institucional da FIOCRUZ (ARCA) |
| repository_id_str |
2135 |
| spelling |
Nair, Divya KMenna-Barreto, F. SSilva Junior, Eufrânio N. daMobin, Shaikh MNamboothiri, Irishi N. N2015-04-17T17:04:30Z2015-04-17T17:04:30Z2014NAIR, Divya K et al. Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes. Chem. Commun.,n.50, p. 6973-6976, 2014.https://www.arca.fiocruz.br/handle/icict/1006110.1039/c4cc02279cengRoyal Society of ChemestryTrypanosoma cruzi,Doença de ChagasTrypanosoma cruzi,Chagas DiseaseChiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleIndian Institute of Technology Bombay. Department of Chemistry. Mombai, India.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ, Brasil.Universidade Federal de Minas Gerais. Departamento de Química. Instituto de Ciências Exatas. Belo Horizonte, MG, Brasil.Indian Institute of Technology Bombay.National Single-Crystal X-Ray Diffraction Facility. Mumbai, India.Indian Institute of Technology Bombay. Department of Chemistry. Mombai, India.Cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes using a quinine derived chiral squaramide organocatalyst led to the formation of pyranones and pyranonaphthoquinones in good to excellent yields and high diastereo- and enantioselectivities. Representative examples of the reaction scale-up with a much lower catalyst loading without an appreciable loss of selectivities and synthetic transformations of the products are also reported here. The compounds described herein for the first time were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, since the structures are related to bioactive α-lapachones.info:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1914https://www.arca.fiocruz.br/bitstream/icict/10061/1/license.txt7d48279ffeed55da8dfe2f8e81f3b81fMD51ORIGINALruben_mennabarretoetal_IOC_2014.pdfapplication/pdf2110264https://www.arca.fiocruz.br/bitstream/icict/10061/2/ruben_mennabarretoetal_IOC_2014.pdf011912cdac92e62c6fe38201213cb0b1MD52TEXTruben_mennabarretoetal_IOC_2014.pdf.txtruben_mennabarretoetal_IOC_2014.pdf.txtExtracted texttext/plain21105https://www.arca.fiocruz.br/bitstream/icict/10061/3/ruben_mennabarretoetal_IOC_2014.pdf.txte4a70e48712f6a5e270618bf98773cbbMD53icict/100612022-06-24 13:08:50.535oai:www.arca.fiocruz.br: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ório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352022-06-24T16:08:50Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes |
| title |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes |
| spellingShingle |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes Nair, Divya K Trypanosoma cruzi, Doença de Chagas Trypanosoma cruzi, Chagas Disease |
| title_short |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes |
| title_full |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes |
| title_fullStr |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes |
| title_full_unstemmed |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes |
| title_sort |
Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes |
| author |
Nair, Divya K |
| author_facet |
Nair, Divya K Menna-Barreto, F. S Silva Junior, Eufrânio N. da Mobin, Shaikh M Namboothiri, Irishi N. N |
| author_role |
author |
| author2 |
Menna-Barreto, F. S Silva Junior, Eufrânio N. da Mobin, Shaikh M Namboothiri, Irishi N. N |
| author2_role |
author author author author |
| dc.contributor.author.fl_str_mv |
Nair, Divya K Menna-Barreto, F. S Silva Junior, Eufrânio N. da Mobin, Shaikh M Namboothiri, Irishi N. N |
| dc.subject.other.pt_BR.fl_str_mv |
Trypanosoma cruzi, Doença de Chagas |
| topic |
Trypanosoma cruzi, Doença de Chagas Trypanosoma cruzi, Chagas Disease |
| dc.subject.en.pt_BR.fl_str_mv |
Trypanosoma cruzi, Chagas Disease |
| description |
Indian Institute of Technology Bombay. Department of Chemistry. Mombai, India. |
| publishDate |
2014 |
| dc.date.issued.fl_str_mv |
2014 |
| dc.date.accessioned.fl_str_mv |
2015-04-17T17:04:30Z |
| dc.date.available.fl_str_mv |
2015-04-17T17:04:30Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.citation.fl_str_mv |
NAIR, Divya K et al. Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes. Chem. Commun.,n.50, p. 6973-6976, 2014. |
| dc.identifier.uri.fl_str_mv |
https://www.arca.fiocruz.br/handle/icict/10061 |
| dc.identifier.doi.pt_BR.fl_str_mv |
10.1039/c4cc02279c |
| identifier_str_mv |
NAIR, Divya K et al. Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes. Chem. Commun.,n.50, p. 6973-6976, 2014. 10.1039/c4cc02279c |
| url |
https://www.arca.fiocruz.br/handle/icict/10061 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
| eu_rights_str_mv |
openAccess |
| dc.publisher.none.fl_str_mv |
Royal Society of Chemestry |
| publisher.none.fl_str_mv |
Royal Society of Chemestry |
| dc.source.none.fl_str_mv |
reponame:Repositório Institucional da FIOCRUZ (ARCA) instname:Fundação Oswaldo Cruz (FIOCRUZ) instacron:FIOCRUZ |
| instname_str |
Fundação Oswaldo Cruz (FIOCRUZ) |
| instacron_str |
FIOCRUZ |
| institution |
FIOCRUZ |
| reponame_str |
Repositório Institucional da FIOCRUZ (ARCA) |
| collection |
Repositório Institucional da FIOCRUZ (ARCA) |
| bitstream.url.fl_str_mv |
https://www.arca.fiocruz.br/bitstream/icict/10061/1/license.txt https://www.arca.fiocruz.br/bitstream/icict/10061/2/ruben_mennabarretoetal_IOC_2014.pdf https://www.arca.fiocruz.br/bitstream/icict/10061/3/ruben_mennabarretoetal_IOC_2014.pdf.txt |
| bitstream.checksum.fl_str_mv |
7d48279ffeed55da8dfe2f8e81f3b81f 011912cdac92e62c6fe38201213cb0b1 e4a70e48712f6a5e270618bf98773cbb |
| bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
| repository.name.fl_str_mv |
Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ) |
| repository.mail.fl_str_mv |
repositorio.arca@fiocruz.br |
| _version_ |
1798324823630282752 |