Copper-Catalyzed Synthesis of Pyrrolo[1,2-c]quinazolines and Pyrrolo[2,1-a]isoquinolines and Antiplasmodial Evaluation
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Nataïlia M Moreira
- Ingrid T de Miranda
- Jhonathan RN dos Santos
- Till Opatz
- Glaucius Oliva
- Rafael VC Guido
- Arlene G Correa
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:001010248800001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.joc.3c00616
- eISSN
- 1520-6904
- Externe Identifier
- Clarivate Analytics Document Solution ID: L1EG4
- PubMed Identifier: 37272775
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 13
- Zeitschrift
- JOURNAL OF ORGANIC CHEMISTRY
- Paginierung
- 8781 - 8790
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Titel
- Copper-Catalyzed Synthesis of Pyrrolo[1,2-<i>c</i>]quinazolines and Pyrrolo[2,1-<i>a</i>]isoquinolines and Antiplasmodial Evaluation
- Sub types
- Article
- Ausgabe der Zeitschrift
- 88
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Natália M Moreira
- Ingrid T de Miranda
- Jhonathan RN dos Santos
- Till Opatz
- Glaucius Oliva
- Rafael VC Guido
- Arlene G Corrêa
- DOI
- 10.1021/acs.joc.3c00616
- eISSN
- 1520-6904
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 13
- Zeitschrift
- The Journal of Organic Chemistry
- Sprache
- en
- Online publication date
- 2023
- Paginierung
- 8781 - 8790
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.joc.3c00616
- Datum der Datenerfassung
- 2023
- Titel
- Copper-Catalyzed Synthesis of Pyrrolo[1,2-<i>c</i>]quinazolines and Pyrrolo[2,1-<i>a</i>]isoquinolines and Antiplasmodial Evaluation
- Ausgabe der Zeitschrift
- 88
Datenquelle: Crossref
- Abstract
- Reactions involving C(sp<sup>3</sup>)-H bonds of azaarenes have been widely studied in recent years as they allow direct functionalization of these <i>N</i>-heterocycles without the use of harsh reaction conditions. In this work, we describe the C(sp<sup>3</sup>)-H functionalization of 4-methylquinazolines and 1-benzylisoquinolines, employing α-substituted β-nitrostyrenes catalyzed by inexpensive copper acetate. Under the optimized condition, 21 pyrrolo[1,2-<i>c</i>]quinazolines, as well as an imidazo[1,2-<i>c</i>]quinazoline and 4 pyrrolo[2,1-<i>a</i>]isoquinolines, were obtained in moderate to good yields. Furthermore, the biological activity of the pyrrolo[1,2-<i>c</i>]quinazolines was evaluated against <i>Plasmodium falciparum</i>, and promising results were obtained.
- Addresses
- Centre of Excellence for Research in Sustainable Chemistry, Chemistry Department, Federal University of São Carlos, São Carlos, São Paulo 13565-905, Brazil.
- Autoren
- Natália M Moreira
- Ingrid T de Miranda
- Jhonathan RN Dos Santos
- Till Opatz
- Glaucius Oliva
- Rafael VC Guido
- Arlene G Corrêa
- DOI
- 10.1021/acs.joc.3c00616
- eISSN
- 1520-6904
- Externe Identifier
- PubMed Identifier: 37272775
- Funding acknowledgements
- Fundação de Amparo à Pesquisa do Estado de São Paulo: 2016/20609-8
- Fundação de Amparo à Pesquisa do Estado de São Paulo: 2017/19940-4
- Fundação de Amparo à Pesquisa do Estado de São Paulo: 2020/12904-5
- Fundação de Amparo à Pesquisa do Estado de São Paulo: 2022/01066-4
- Conselho Nacional de Desenvolvimento Científico e Tecnológico: 429748/2018-3
- Fundação de Amparo à Pesquisa do Estado de São Paulo: 2014/50249-8
- Conselho Nacional de Desenvolvimento Científico e Tecnológico: 302140/2019-0
- GlaxoSmithKline:
- Fundação de Amparo à Pesquisa do Estado de São Paulo: 2020/10349-4
- Fundação de Amparo à Pesquisa do Estado de São Paulo: 2013/07600-3
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior: 001
- Open access
- false
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 13
- Zeitschrift
- The Journal of organic chemistry
- Schlüsselwörter
- Copper
- Isoquinolines
- Quinazolines
- Antimalarials
- Catalysis
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2023
- Paginierung
- 8781 - 8790
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Datum der Datenerfassung
- 2023
- Titel
- Copper-Catalyzed Synthesis of Pyrrolo[1,2-<i>c</i>]quinazolines and Pyrrolo[2,1-<i>a</i>]isoquinolines and Antiplasmodial Evaluation.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 88
Datenquelle: Europe PubMed Central
- Abstract
- Reactions involving C(sp3)-H bonds of azaarenes have been widely studied in recent years as they allow direct functionalization of these N-heterocycles without the use of harsh reaction conditions. In this work, we describe the C(sp3)-H functionalization of 4-methylquinazolines and 1-benzylisoquinolines, employing α-substituted β-nitrostyrenes catalyzed by inexpensive copper acetate. Under the optimized condition, 21 pyrrolo[1,2-c]quinazolines, as well as an imidazo[1,2-c]quinazoline and 4 pyrrolo[2,1-a]isoquinolines, were obtained in moderate to good yields. Furthermore, the biological activity of the pyrrolo[1,2-c]quinazolines was evaluated against Plasmodium falciparum, and promising results were obtained.
- Autoren
- Natália M Moreira
- Ingrid T de Miranda
- Jhonathan RN Dos Santos
- Till Opatz
- Glaucius Oliva
- Rafael VC Guido
- Arlene G Corrêa
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/37272775
- DOI
- 10.1021/acs.joc.3c00616
- eISSN
- 1520-6904
- Ausgabe der Veröffentlichung
- 13
- Zeitschrift
- J Org Chem
- Schlüsselwörter
- Quinazolines
- Copper
- Antimalarials
- Isoquinolines
- Catalysis
- Sprache
- eng
- Country
- United States
- Paginierung
- 8781 - 8790
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2023
- Titel
- Copper-Catalyzed Synthesis of Pyrrolo[1,2-c]quinazolines and Pyrrolo[2,1-a]isoquinolines and Antiplasmodial Evaluation.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 88
Datenquelle: PubMed
- Beziehungen:
- Eigentum von