Cp*Rh-Catalyzed Sulfonamide-Directed Ortho Arene C-H Carbenoid Functionalization with Pyridotriazoles.

Org Lett

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica , Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050 , China.

Published: February 2020

In this Letter, triazoles as carbene reagents were used for sulfonamide-directed C-H insertion carbenoid functionalization to construct benzylpyridine sulfonamide dual-pharmacophore compounds. This method is simple and efficient and can be used for the late-stage modification of sulfonamide drugs.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.9b03904DOI Listing

Publication Analysis

Top Keywords

carbenoid functionalization
8
cp*rh-catalyzed sulfonamide-directed
4
sulfonamide-directed ortho
4
ortho arene
4
arene c-h
4
c-h carbenoid
4
functionalization pyridotriazoles
4
pyridotriazoles letter
4
letter triazoles
4
triazoles carbene
4

Similar Publications

In this study, we report the first example of acyclic (amino)(N-pyridinium)carbenoid gold(III) complexes synthesized via a coupling reaction between 2-pyridylselenyl chloride and Au(I)-bound isonitriles. The reaction involves an initial oxidative addition of the Se-Cl moiety to Au(I), followed by the nucleophilic addition of the pyridine fragment to the isonitrile's C≡N bond, furnishing a metallacycle. Importantly, this is the first example of the pyridine acting as a nucleophile towards metal-bound isonitriles.

View Article and Find Full Text PDF

The relative reactivity and cis/trans selectivity of the intramolecular [3+2] cycloaddition (IM32CA) reactions of nitrile oxide (NO), azide (AZ), nitrile sulfide (NS) and nitrile ylide (NY), leading to functionalized heterocycles are studied within the Molecular Electron Density Theory. The kinetically controlled IM32CA reactions are predicted to be cis stereospecific, while the reaction feasibility follows the order NY>NS>NO>AZ with the respective activation Gibbs free energies of 13.7, 17.

View Article and Find Full Text PDF

Rh(II)/Pd(0) Dual Catalysis: Carbenoid N-H Insertion/Allylation Cascade Reaction to Construct Highly Functionalized and Polysubstituted Pyrrolidines.

Molecules

December 2024

State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School of Chemistry and Chemical Engneering, Shihezi University, Shihezi 832003, China.

In the category of drugs approved by the U.S. FDA, pyrrolidine is the most frequently used core of five-membered nonaromatic heterocycles containing nitrogen.

View Article and Find Full Text PDF

The chemoselective synthesis of trisubstituted alkenyl halides (Cl, Br, F, I) starting from ketones and aldehydes and lithium halocarbenoids is reported. Upon forming the corresponding tetrahedral intermediate adduct, followed by the addition of thionyl chloride, a selective E2-type elimination is triggered, furnishing the targeted motifs. The transformation takes place under full chemocontrol: various sensitive functionalities ( ester, nitrile, nitro, or halogen groups) can be placed on the starting materials, thus documenting a wide reaction scope, as well as the application of the technique to biologically active substances.

View Article and Find Full Text PDF

Solvent-Controlled Rh(III)-Catalyzed Mono- and Dual Functionalization of Quinolyl Aldoximes with Diazo Compounds.

J Org Chem

December 2024

Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.

A solvent-controlled Rh(III)-catalyzed mono- and dual-C-H bond activation/carbene migratory insertion with diazo compounds as a single coupling partner was demonstrated. The reaction proceeded under mild conditions, yielding products in good to excellent yields. These results are significant for the development of the domino multiple functionalization of C(sp)-H bonds via a carbenoid insertion approach.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!