4.5 Article

Synthesis of 2-Azetidinones Incorporating Carbenechromium(0) Moieties and Their Use in the Preparation of Penicillin- and Cephalosporin-Containing Peptides

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2009, 期 18, 页码 2998-3005

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900188

关键词

-

资金

  1. Spanish Ministerio de Educacion y Ciencia (MEC) [CTQ2007-67730-C02-01/BQU, CSD2007-0006]
  2. Comunidad Autonoma de Madrid [CCG07-UCM-PPQ-2596]
  3. MEC

向作者/读者索取更多资源

A series of beta-lactams incorporating a carbenechromium(0) moiety in their structures have been prepared. These stable compounds are suitable precursors for the preparation of alpha-amino esters, dipeptides and tripeptides tethered to a 2-azetidinone ring. The methodology has also been extended to the synthesis of carbenechromium(0) complexes of penicillin G, cephalosporin and 6-aminopenicillanic acid. All these new metalla-beta-lactam derivatives are stable compounds and can be transformed into antibiotic structures with tripeptide side-chains. The methodology relies on the compatibility of the beta-lactam ring with the carbenechromium(0) moiety and on the stability of the four-membered ring during the photocarbonylation of the resulting chromium complex. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.5
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Polymer Science

Acidic triggering of reversible electrochemical activity in a pyrenetetraone-based 2D polymer

Paloma Garcia-Arroyo, Paula Navalpotro, Maria J. Mancheno, Elena Salagre, Jorge J. Cabrera-Trujillo, Enrique G. Michel, Jose L. Segura, Javier Carretero-Gonzalez

Summary: In this study, a novel two-dimensional polymer network, DAPT-TFP, was successfully synthesized and shown to exhibit high thermal and chemical stability. An application to conductive additive-free electrode demonstrated the potential of the material, with improved performance of the nanostructure through simple acidic treatment.

POLYMER (2021)

Article Chemistry, Inorganic & Nuclear

Preparation and Degradation of Rhodium and Iridium Diolefin Catalysts for the Acceptorless and Base-Free Dehydrogenation of Secondary Alcohols

Maria L. Buil, Alba Collado, Miguel A. Esteruelas, Mar Gomez-Gallego, Susana Izquierdo, Antonio Nicasio, Enrique Onate, Miguel A. Sierra

Summary: Rhodium and iridium diolefin catalysts are used for the acceptorless and base-free dehydrogenation of secondary alcohols, and their degradation during the reactions has been investigated. The study of the reactivity of the dimers has shown complex structural changes.

ORGANOMETALLICS (2021)

Article Chemistry, Multidisciplinary

Role of imine isomerization in the stereocontrol of the Staudinger reaction between ketenes and imines

Fernando P. Cossio, Abel de Cozar, Miguel A. Sierra, Luis Casarrubios, Jaime G. Muntaner, Bimal K. Banik, Debasish Bandyopadhyay

Summary: Computational-experimental analysis has determined that the stereochemistry of the Staudinger reaction is closely associated with the nature of the imine, affecting the nucleophilic attack and electrocyclization steps. The impact of energetically accessible in situ isomerization patterns and substituents of the imine on the reaction's stereochemistry has been analyzed kinetically, with results supporting experimental findings.

RSC ADVANCES (2021)

Article Chemistry, Inorganic & Nuclear

Two Complementary Approaches to Silicon-Supported Soluble [FeFe]-Hydrogenase Mimics

Sergio Aguado, Diego J. Vicent, Luis Casarrubios, Carmen Ramirez de Arellano, Miguel A. Sierra

Summary: This study prepared two series of silicon-supported hydrogenase mimics and nanostructures containing multiple mimics. These compounds were characterized and studied for their electrochemical properties. The results showed that these compounds were soluble in organic solvents and exhibited stable electrochemical behavior and electrocatalytic activity. Additionally, the integrity of the silicon cage was maintained even in the presence of acetic acid.

ORGANOMETALLICS (2022)

Article Chemistry, Inorganic & Nuclear

Heteropolymetallic [FeFe]-Hydrogenase Mimics: Synthesis and Electrochemical Properties

Alejandro Torres, Alba Collado, Mar Gomez-Gallego, Carmen Ramirez de Arellano, Miguel A. Sierra

Summary: In this study, tetranuclear [Fe2S2] hydrogenase mimic complexes containing Pt(II), Ni(II), and Ru(II) complexes were synthesized and their electrochemical properties were investigated. The incorporation of metal complexes in the structure modulated the electronic communication between the redox-active [Fe2S2] centers. Specifically, the structure of the phosphine ligand in the Pt compounds played a crucial role in facilitating or hindering the electronic communication, while the addition of a Ru-bis(bipyridine) complex promoted the communication. These experimental and computational findings provide insights into the electronic interaction between redox-active centers in hydrogenase.

INORGANIC CHEMISTRY (2023)

Article Chemistry, Inorganic & Nuclear

Synthesis, Structure, and Photophysical Properties of Platinum(II) (N,C,N') Pincer Complexes Derived from Purine Nucleobases

Carmen Lorenzo-Aparicio, Sonia Moreno-Blazquez, Montserrat Olivan, Miguel A. Esteruelas, Mar Gomez Gallego, Pablo Garcia-Alvarez, Javier A. Cabeza, Miguel A. Sierra

Summary: The synthesis of Pt pincer complexes derived from purine and purine nucleosides is reported. The complexes have different coordination points due to the structure of the purine skeleton and substituents on the phenyl ring. The complexes show regioselectivity and have potential applications as interstrand cross-linking models.

INORGANIC CHEMISTRY (2023)

Article Chemistry, Inorganic & Nuclear

Phosphite Bearing [(μ-ADT)RFe2(CO)6] (ADT = Azadithiolate) Moieties: A Tool for the Building of Multimetallic [FeFe]- Hydrogenase Mimics

Alejandro Torres, Diego J. Vicent, Alba Collado, Mar Gomez-Gallego, Carmen Ramirez de Arellano, Miguel A. Sierra

Summary: A new phosphite ligand with three [(mu-ADT)RFe2(CO)6] (R= p-HOC6H4) moieties (2) was successfully synthesized by the reaction of [(mu-ADT)RFe2(CO)6] (R= p-HOC6H4) 1a with PCl3. Coordination of this phosphite to [PdCl2(MeCN)2] or [PtCl2(DMSO)2] resulted in the formation of heterometallic square planar complexes 5. Reaction of phosphite 2 with [MCl2Cp*]2 (M = Rh, Ir) yielded three-legged piano stool complexes 6. The versatility of this new ligand in forming different heteropolymetallic complexes under mild reaction conditions was demonstrated by the formation of complexes 5 and 6.

ORGANOMETALLICS (2023)

Article Chemistry, Physical

On the Mechanism and Selectivity of Palladium-Catalyzed C(sp3)-H Arylation of Pyrrolidines and Piperidines at Unactivated C4 Positions: Discovery of an Improved Dimethylaminoquinoline Amide Directing Group

Daniele Antermite, Andrew J. P. White, Luis Casarrubios, James A. Bull

Summary: This study presents a combined experimental and computational investigation on the regio- and stereoselective C4 arylation of pyrrolidines and piperidines using C3 aminoquinoline amide directing groups. The mechanistic experiments reveal a cis-selective pathway and the discovery of an improved directing group. This study contributes to the understanding and improvement of C-H functionalization of N-heterocycles.

ACS CATALYSIS (2023)

Article Chemistry, Organic

β-Lactam and penicillin substituted mesoionic metal carbene complexes

Marta G. Avello, Maria Moreno-Latorre, Maria C. de la Torre, Luis Casarrubios, Heinz Gornitzka, Catherine Hemmert, Miguel A. Sierra

Summary: Triazolylidene MIC M-complexes (M = Au, Pd, Pt) with 2-azetidinones and penicillin G substituents at the triazole ring were synthesized and their catalytic properties were investigated.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Inorganic & Nuclear

Phosphorescent Ir(III) complexes derived from purine nucleobases

Carmen Lorenzo-Aparicio, Mar Gomez Gallego, Carmen Ramirez de Arellano, Miguel A. Sierra

Summary: In this study, new types of neutral and cationic phosphorescent complexes derived from 6-phenylpurine nucleosides and nucleotides were prepared and studied. The neutral complexes exhibit orange-red emission upon photoexcitation, while the cationic complexes emit yellow-green light.

DALTON TRANSACTIONS (2022)

Article Chemistry, Multidisciplinary

Electrocatalytic Behavior of Tetrathiafulvalene (TTF) and Extended Tetrathiafulvalene (exTTF) [FeFe] Hydrogenase Mimics

Alejandro Torres, Alba Collado, Mar Gomez-Gallego, Carmen Ramirez de Arellano, Miguel A. Sierra

Summary: TTF and exTTF-containing complexes were prepared by the photochemical reaction with [(??-S2)Fe2(CO)6]. These complexes can interact with PAHs, and exhibit an electrocatalytic dihydrogen evolution reaction under certain conditions. The presence of air influences the electrochemistry of these systems, suggesting potential for the design of hydrogenase mimics combining the properties of [FeFe] cores with unique TTF properties.

ACS ORGANIC & INORGANIC AU (2022)

Review Chemistry, Inorganic & Nuclear

Deuteration mechanistic studies of hydrogenase mimics

Mar Gomez-Gallego, Miguel A. Sierra

Summary: Hydrogen production is crucial for carbon-free energy production, and using hydrogenase mimics is an important approach to enhance efficiency. The use of isotopes, such as deuterium, can help unravel key steps in hydrogen generation mechanisms.

INORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Multidisciplinary

Single-molecule conductance in a unique cross-conjugated tetra(aminoaryl)ethene

Samara Medina Rivero, Paloma Garcia Arroyo, Liang Li, Suman Gunasekaran, Thijs Stuyver, Maria Jose Mancheno, Mercedes Alonso, Latha Venkataraman, Jose L. Segura, Juan Casado

Summary: Experimental and modeling studies have shown that 1,1,2,2-tetrakis(4-aminophenyl)ethene can form molecular junctions with gold electrodes for single-molecule conductance measurements, exhibiting only two regimes of conduction. The linear transmission is achieved through-bond, while the cross-conjugated channel is further assisted by through-space transmission, partially alleviating destructive quantum interference.

CHEMICAL COMMUNICATIONS (2021)

暂无数据