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Maqueda-Zelaya et al. The Journal of Organic Chemistry. 2023;88(19):14131 -14139. 1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives.

Publicaciones > Maqueda-Zelaya et al

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

Resumen

No hay resumen

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

XXV EuCOMC, XXV CONFERENCE ON ORGANOMETALLIC CHEMISTRY

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

Zurro et al. European Journal of Organic Chemistry. 2023;e202300535. Visible-light mediated synthesis of bicalutamide by regioselective hydroxysulfonylation of acrylamides.

Publicaciones > Zurro et al

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

Resumen

No hay resumen

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.

Altarejos et al. J Org Chem. 2023;:. One-Pot (3 + 2) Cycloaddition-Isomerization-Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives.

Publicaciones > Altarejos et al

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

1. Universidad de Alcalá, Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), 28805, Alcala de Henares, Madrid, Spain.  2. Instituto Ramón y Cajal de Investigación Sanitaria (IRYCIS) 28034, Madrid, Spain.

Abstract

A facile access to 5-aryl-3-trifluoromethylpyrazoles has been developed by a one-pot (3 %@2B 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, 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.

Señorans et al. ACS Macro Lett. 2023;12(7):949-954. Hyper-Cross-Linked Porous Polymer Featuring B-N Covalent Bonds (HCP-BNs): A Stable and Efficient Metal-Free Heterogeneous Photocatalyst.

Publicaciones > Señorans et al

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

1. Department of Frontiers in Materials Chemistry, Instituto de Ciencia de Materiales de Madrid (ICMM-CSIC), Sor Juana Inés de la Cruz, 3, Cantoblanco, Madrid 28049, Spain.  2. Universidad de Alcalá (IRYCIS), Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Campus Científico-Tecnológico, Facultad de Farmacia, Autovía A-II, Km 33.1, 28805-Alcalá de Henares, Madrid, Spain.

Abstract

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 S(BET) of 612 m(2)/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.