Ciudad Real (Spain), 18 – 91 November
The Chemical Biology Group from the University of Alcalá was well represented in the Young Research Symposium of the Spanish Royal Society of Chemistry hold in the city of Ciudad Real.
– Flash + Poster:
· Modulating the pseudokinase integrin-linked kinase through new small molecules
Marta Durán, Mercedes Griera Merino, Ana María Carozo, Sergio de Frutos García, José Luis Aceña, Laura Calleros, Diego Rodríguez Puyol, Javier García-Marín
– Poster:
· 1,1-Diamine scaffold synthesis under visible light irradiation
Guillermo Morales-Ortega, Javier Carreras
– Poster:
· Acid-mediated synthesis of fluorescent functionalized polycycles via catiionic cyclization of o-acryloyl-o’alkynylbiaryls
Alex Hipólito-Barriuso, Patricia García-García, Manuel Á. Fernández-Rodgríguez
Our research group members, Álvaro González and Clara Mañas were at the recent doctoral hooding ceremony at the University of Alcalá. Accompanied by their thesis advisors,Dr. Juan J. Vaquero and Dr. Estíbaliz Merino, they celebrated the achievements of the new Ph.D. recipients.
Congrats!!
Clara Mañas, Estíbaliz Merino*
We disclose the intramolecular synthesis of 3-alkenyl-2<i>H</i>-indazoles from 2-alkynylazobenzenes promoted by a dual catalysis using AuCl3 and a ruthenium photocatalyst under irradiation with visible light. This reaction goes through a hydroamination of the alkynyl fragment. The yields are governed by the electronic factors. Control experiments and DFT calculations suggest that a radical and polar mechanisms are operating in parallel. This transformation goes through first formation and C-N bond and 1,2-hydride shift. Derivatization was also carried out to extend the versatility of this methodology.
Adv. Synth. Cat. 2024
DOI: 10.1002/adsc.202400990
Clara Mañas, Juan Herrero-Bourdieu, Estíbaliz Merino*
A copper-catalyzed intramolecular synthesis of 3-alkenyl-2H-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C–N bond formation and a subsequent 1,2-hydride shift, affording products in high yields. DFT calculations suggest the 1,2-hydride shift as the rate-determining step. Further derivatization enables functionalization of the 3-alkenyl-2H-indazoles.
J. Org. Chem. 2024.
DOI: 10.1021/acs.joc.4c02144
Clara Mañas, Ana Belén Ibarra, Estíbaliz Merino*
The development of regiodivergent methods that allow access to different structures from a single substrate through intramolecular processes is crucial for accelerating new molecule discovery, as well as making processes more sustainable and efficient in terms of waste production and economy. In this study, we report a novel regiodivergent cyclization procedure to access two distinct azapolyaromatic regioisomers from 2-alkynylazobenzenes. The key to achieving this regiodivergence lies in the presence or absence of a gold catalyst. The irradiation with visible light of 2-alkynylazobenzenes in the presence of a Ir photocatalyst affords 11H-indolo[1,2-b]indazoles, whereas under similar conditions with AuCl3, indazolo[2,3-a]quinolines are produced. Control experiments and DFT calculations suggest that both transformations operate through different reaction mechanisms: the formation of 11H-indolo[1,2-b]indazoles involves a radical mechanism, whereas the formation of indazolo[2,3-a]quinolines appears to proceed predominantly through a polar mechanism. This transformation enables the one-step conversion of simple 2-alkynylazobenzenes into diverse azapolyaromatic structures via an intramolecular visible light-promoted process, holding significant potential for new nitrogenated heterocycles.
Org. Chem. Front. 2024.
DOI: 10.1039/d4qo01606h
orcid.org/0009-0000-5684-1261