NHC-Catalyzed [2 + 4] Annulation of Alkynyl Ester with Chalcone.

J Org Chem

Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China.

Published: May 2022

An NHC-catalyzed [2 + 4] cyclization of alkynyl ester with α,β-unsaturated ketone to form a pyran scaffold was developed successfully. The cheap and easily available starting materials, mild reaction conditions, moderate to excellent yields, and high atom economy make this strategy attractive for the syntheses of highly substituted 4-pyran derivatives.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.2c00022DOI Listing

Publication Analysis

Top Keywords

alkynyl ester
8
nhc-catalyzed annulation
4
annulation alkynyl
4
ester chalcone
4
chalcone nhc-catalyzed
4
nhc-catalyzed cyclization
4
cyclization alkynyl
4
ester αβ-unsaturated
4
αβ-unsaturated ketone
4
ketone form
4

Similar Publications

Regioselective [3 + 2] Annulation of β,γ-Alkynyl-α-ketimino Esters with 1,3-Dicarbonyls: The Synthesis of Highly Functionalized Dihydrofurans.

J Org Chem

January 2025

Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, Laboratory of Optic-electric Chemo/Biosensing and Molecular Recognition, Education Department of Guangxi Zhuang Autonomous Region, Guangxi Minzu University, Nanning 530006, China.

A regioselective [3 + 2] annulation of β,γ-alkynyl-α-ketimino esters with 1,3-dicarbonyls is disclosed. A series of -selective dihydrofurans bearing an exocyclic double bond and a quaternary carbon center are accessed without the usage of base. Control and deuterium-labeling experiments have been investigated to probe into the reaction mechanism.

View Article and Find Full Text PDF

One-Pot Synthesis of 2-Substituted Indoles and 7-Azaindoles Sequential Alkynylation and Cyclization of 2-Iodo--mesylarylamines and Alkynes in the Presence of CuO.

Asian J Org Chem

January 2025

Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, New Jersey 08854, USA.

A one-pot process was developed to synthesize in moderate to high yield a series of 2-substituted indoles and 7-azaindoles starting from 2-iodo--mesylarylamines and terminal alkynes in the presence of CuO in DMF at 90-120 °C. Without isolation of any intermediate, our optimized conditions enabled the introduction of ester, phenyl, hydroxymethyl, hydroxyethyl, -Boc-aminomethyl, and methyl at the 2-postion of indoles and 7-azaindoles. The reaction tolerates a variety of substrates containing halogens, or acid- or base-sensitive functional groups without requiring a Pd catalyst, a ligand, or a base.

View Article and Find Full Text PDF

Palladium-Catalyzed Solvent-Controlled Divergent C2/C5 Site-Selective Alkynylation of Pyrrole Derivatives.

J Org Chem

January 2025

Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, China.

Among the known aromatic -heterocycles, pyrroles are significant and versatile privileged components in pharmacologically relevant molecules. Herein, we demonstrate a protocol for the selective construction of alkynylated pyrroles in a diversity-oriented fashion through divergent C2/C5 site-selective alkynylation of pyrrole derivatives by employing a palladium catalyst with two different solvent systems. In the presence of 1,4-dioxane, the C2-alkynylation process via chelation-assisted palladation is favored.

View Article and Find Full Text PDF

Copper-Catalyzed Asymmetric Nucleophilic Opening of 1,1,2,2-Tetrasubstituted Donor-Acceptor Cyclopropanes for the Synthesis of α-Tertiary Amines.

J Am Chem Soc

January 2025

State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China.

Article Synopsis
  • The catalytic asymmetric transformation of donor-acceptor cyclopropanes (DACs) is an important method for creating a variety of enantioenriched molecules, but using tetrasubstituted DACs to generate products with quaternary stereocenters has been a persistent challenge.
  • This study introduces a copper-catalyzed asymmetric aminative ring-opening process for tetrasubstituted alkynyl DACs that successfully produces a wide range of α-tertiary amines with high enantioselectivity.
  • The resulting products, which contain alkyne, amine, and ester groups, open up new possibilities for synthesizing bioactive molecules, with mechanism studies highlighting the significance of a zwitter
View Article and Find Full Text PDF

Base-promoted cascade 5- annulation/carboxylation of -(1-alkynyl)benzenesulfonamides with CO: divergent synthesis of mono- or -dicarboxylic esters.

Chem Commun (Camb)

December 2024

Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.

A base-promoted cascade 5- cyclization/carboxylation of -alkynylsulfamides with CO has been accomplished, furnishing a variety of benzosultam-containing acrylates in good yields by using CO as the carboxylic source. Notably, in the case of substrates bearing a TMS-alkyne motif, the -dicarboxylation products were generated unprecedentedly.

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!