A new strategy for thiazoles via copper-catalyzed [3+1+1]-type condensation reaction from oximes, anhydrides and potassiumthiocyanate (KSCN) is developed herein. The transformation has good functional group tolerance and various thiazoles were formed smoothly in good to excellent yields under mild reaction conditions. This process involves copper-catalyzed N-O/C-S bond cleavages, activation of vinyl sp C-H bond, and C-S/C-N bond formations which are under redox-neutral conditions as well as operational simplicity.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.6b02124DOI Listing

Publication Analysis

Top Keywords

copper-catalyzed [3+1+1]-type
8
[3+1+1]-type condensation
8
condensation reaction
8
redox-neutral conditions
8
access thiazole
4
thiazole copper-catalyzed
4
reaction redox-neutral
4
conditions strategy
4
strategy thiazoles
4
thiazoles copper-catalyzed
4

Similar Publications

Synthesis of an Azido-Substituted 8-Membered Ring Laddersiloxane and Its Application in Catalysis.

Molecules

January 2025

ICGM, Univ Montpellier, CNRS, ENSCM (Institut Charles Gerhardt Montpellier, Université de Montpellier, Centre National de la Recherche Scientifique, École Nationale Supérieure de Chimie de Montpellier), 1919 Route de Mende, CEDEX 05, 34293 Montpellier, France.

A first -type tricyclic 8-8-8 (three fused-8-membered ring) laddersiloxane functionalized with four azido groups was successfully synthesized through efficient and highly selective hydrosilylation and nucleophilic substitution, achieving an excellent overall yield. The starting material, a tetravinyl-substituted 8-8-8 laddersiloxane, was prepared via a straightforward and scalable method. The obtained azido-functionalized ladder compound, fully characterized, constitutes a versatile building block for hybrid materials.

View Article and Find Full Text PDF

Our efforts toward the synthesis of the marine natural product portimine are described. The key to the synthesis of the skeleton is a stereoretentive copper-catalyzed C()-C() Stille-type cross-coupling that enables the convergent assembly of functionalized fragments. The core skeleton of portimine was constructed via ring-closing metathesis and transannular acetal formation.

View Article and Find Full Text PDF

Copper-Catalyzed Enantioselective Skeletal Editing through a Formal Nitrogen Insertion into Indoles to Synthesize Atropisomeric Aminoaryl Quinoxalines.

Angew Chem Int Ed Engl

December 2024

State key laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin, 541004, China.

Skeletal editing represents an attractive strategy for adding complexity to a given molecular scaffold in chemical synthesis. Isodesmic reactions provide a complementary skeletal editing approach for the redistribution of chemical bonds in chemical synthesis. However, catalytic enantioselective isodesmic reaction is extremely scarce and enantioselective isodesmic reaction to synthesize atropisomeric compounds is unknown.

View Article and Find Full Text PDF

The importance of lectins in biological processes such as pathogen recognition, cell adhesion, and cell recognition is well documented. C-Type lectins, which require calcium for binding, play an important role in the innate immune response by engaging carbohydrates presented as part of the human and pathogen glycocalyx. For example, lectins such as MBL, Dectin-2, langerin and DC-SIGN selectively recognize mannose rich (high-mannose) structures presented as part of the glycocalyx.

View Article and Find Full Text PDF

Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes.

Nat Commun

October 2024

State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China.

The asymmetric Büchner reaction and related arene cyclopropanations represent one type of the powerful methods for enantioselective dearomatization. However, examples of asymmetric Büchner reactions via a non-diazo approach are quite scarce, and the related arene cyclopropanation based on alkynes has not been reported. Herein, we disclose an asymmetric Büchner reaction and the related arene cyclopropanation by copper-catalyzed controllable cyclization of N-propargyl ynamides via vinyl cation intermediates, leading to chiral tricycle-fused cycloheptatrienes and benzonorcaradienes in high yields and enantioselectivities.

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!