Archivo de la categoría: Noticias

Nuevo artículo, J. Org. Chem. 09.23

1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives

Francisco Maqueda-Zelaya, José Luis Aceña*, Estíbaliz Merino, Juan J. Vaquero, and David Sucunza*

J. Org. Chem. 2023, ASAP
DOI: 10.1021/acs.joc.3c01675

An efficient methodology to form 4-alkoxy- and 4-aryloxybenzo[d][1,2,3]triazines via an intramolecular heterocyclization of 1-azido-2-[isocyano(p-tosyl)methyl]benzenes under basic conditions has been developed. DFT calculations have been performed to further understand the mechanism of this heterocyclization, which occurs in good to excellent yields with a broad scope.

Participación XXV EuCOMC


Alcalá de Henares, 4 – 8 septiembre

– Póster:
· Copper-catalyzed intramolecular cyclization of alkynylazobenzenes for the synthesis of 2H-indazoles
Clara Mañas, Juan Herrero, Estíbaliz Merino

– Póster:
· Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides
Guillermo G. Otárola, Mercedes Zurro, Sergio Torres-Oya, Juan José Vaquero, Estíbaliz Merino

– Póster:
· Direct conversion of C1−C6 alkanes into trifluoromethyl derivatives
Jonathan Martínez-Laguna, M. Ángeles Fuentes, Julia Altarejos, Javier Carreras, Ana Caballero, Pedro J. Pérez

Nuevo artículo, Eur. J. Org. Chem. 08.23

Visible-light mediated synthesis of bicalutamide by regioselective hydroxysulfonylation of acrylamides

Mercedes Zurro, Sergio Torres-Oya, Estíbaliz Merino*

Eur. J. Org. Chem. 2023, Accepted Articles
DOI: 10.1002/ejoc.202300535

Synthesis of anticancer drug bicalutamide promoted by visible light in one step from the corresponding N-arylacrylamide is described. This approach involves a one-pot hydroxysulfonylation reaction via a photocatalytic redox process. The use of Na2Eosin Y as photocatalyst and blue light allows the access to a broad range of α-hydroxysulfonylamides bearing a quaternary center in moderate to good yields with complete regioselectivity via radical process.

Nuevo artículo, J. Org. Chem. 07.23

One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives

Julia Altarejos, Estíbaliz Merino, David Sucunza, Juan J. Vaquero, and Javier Carreras*

J. Org. Chem. 2023, ASAP
DOI: 10.1021/acs.joc.3c00396

A facile access to 5-aryl-3-trifluoromethylpyrazoles has been developed by a one-pot (3 + 2) cycloaddition–isomerization–oxidation sequence employing 2,2,2-trifluorodiazoethane and styryl derivatives. A broad variety of functional groups and good yields are achieved under mild conditions. Additionally, the functionalization of 3-trifluoromethylpyrazoles was studied. DFT calculations of the cycloaddition transition state energies are consistent with the experimentally observed reactivity.

Nuevo artículo, Adv. Synth. Cat. 07.23

β-Functionalization of 4a-aza-8a-boranaphthalene via Iridium-catalyzed C−H Borylation

Isabel Valencia, David Sucunza, Francisco Mendicuti, Patricia García-García,* Juan J. Vaquero

Adv. Synth. Cat. 2023, Accepted Articles
DOI: 10.1002/adsc.202300408

A general method for the functionalization of 4a-aza-8a-boranaphthalene in the position β to the nitrogen atom has been developed. This method is based on a regioselective iridium-catalyzed C−H activation process for the introduction of a boronate group, which can subsequently be transformed into a variety of aryl or alkynyl groups via cross-coupling reactions. Selective mono- or difunctionalization can be achieved by controlling the reaction conditions during the borylation step. The photophysical properties of the obtained 3- or 3,6-substituted BN-naphthalenes have been evaluated, and some of them have been found to be significantly fluorescent, with fluorescence quantum yields up to 0.85.

Participación congresos

23rd Tetrahedron Symposium

Gothenburg, Sweden, 27 – 30 junio

– Póster:
· Visible light as a single reagent to promote new transformations in azobenzenes
Clara Mañas, Estíbaliz Merino

– Póster:
· Synthesis of 5-aryl-3-trifluoromethylpyrazoles: one-pot [3+2] cycloaddition-isomerization-oxidation
Julia Altarejos, Estíbaliz Merino, David Sucunza, Juan José Vaquero, Javier Carreras

– Póster:
· Synthesis of borylated polycycles by metal-free borylative cyclization of enynes
Ana Milián, Ester Sans-Panadés, Marcos Humanes, Cintia Virumbrales, Estíbaliz Merino, Roberto Sanz, Juan J. Vaquero, Manuel A. Fernández-Rodríguez, Patricia García-García

– Póster:
· Ir-Catalyzed C−H Borylation of 4a,8a-Dihydro-4a-Aza-8a-Boranaphthalene
Isabel Valencia, Patricia Garcia-Garcia, David Sucunza, Francisco Mendicuti, Juan J. Vaquero

XXXIX Reunión Bienal de la RSEQ

Zaragoza, 27 – 30 junio

– Póster:
· Visible Light Na2Eosin Y Catalysed Hydroxysulfonylation of Acrylamides. Straightforward Access to Anticancer Drug Bicalutamide
Mercedes Zurro, Sergio Torres-Oya, Estibaliz Merino*

– Póster/Flash:
· BF3-promoted cascade cyclization of biaryl embedded 1,8-enynes
Jaime Tostado, Juan J. Vaquero, Manuel A. Rodríguez

– Póster:
· Synthesis of benzo[1.2.3]triazines by heterocyclization of TOSMIC derivatives
Francisco Maqueda, David Sucunza, José Luis Aceña, Juan José Vaquero

– Póster/Flash:
· Synthesis of polycyclic hydrocarbons by gold-catalyzes tandem formation of 4-, 5- and 7-membered rings
L. Sánchez-Jiménez, A. Gargantiel, P. García-García, M. A. Fernández-Rodríguez

– Póster/Flash:
· Towards new peptide-based compounds: synthesis of a series of novel bicyclic amino acids
Álvaro González-Molina, José Luis Aceña y Juan José Vaquero

– Póster/Flash:
· New photoreactivity of azobenzenes towards complex N-heterocycles
Clara Mañas, Estíbaliz Merino

IX Symposium of Medicinal Chemistry Young Researchers

Santiago de Compostela, 22 junio

· Novel bicyclic amino acids as potential building blocks for new peptidomimetics
Álvaro González-Molina, José Luis Aceña y Juan José Vaquero

Nuevo artículo, ACS Macro Lett. 06.2023

Hyper-Cross-Linked Porous Polymer Featuring B–N Covalent Bonds (HCP-BNs): A Stable and Efficient Metal-Free Heterogeneous Photocatalyst

Sara Señorans, Isabel Valencia, Estíbaliz Merino, Marta Iglesias, Manuel A. Fernández-Rodríguez*, Eva M. Maya*

ACS Macro Lett. 2023, ASAP
DOI: 10.1021/acsmacrolett.3c00217

The first example of a porous polymer containing B–N covalent bonds, prepared from a tetraphene B–N monomer and biphenyl as a comonomer, is reported. It was prepared using the solvent knitting strategy, which allows the connection between the aromatic rings of the two monomers through methylene groups provided by an external cross-linking agent. The new polymer exhibited micromeso porosity with an SBET of 612 m2/g, high thermal stability, and potential properties as a heterogeneous photocatalyst, since it is very active in the aza-Henry coupling reaction (>98% of conversion and selectivity). After the first run, the catalyst improves its photocatalytic activity, shortening the reaction time to only 2 h and maintaining this activity in successive runs. The presence of a radical in this structure that remains stable with successive runs makes it a new type of material with potential applications as a highly stable and efficient photocatalyst.