A copper-catalyzed decarboxylative cascade cyclization of propargylic cyclic carbonates/carbamates with pyridinium 1,4-zwitterionic thiolates is developed. A range of fused polyheterocyclic compounds are obtained in moderate to good yields with excellent diastereoselectivities. Of particular note is that four new bonds (two C-C, one C-O/N, one C-S) and four new stereocenters could be efficiently embedded into the tetracyclic fused scaffolds in a single step.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.2c01959DOI Listing

Publication Analysis

Top Keywords

copper-catalyzed decarboxylative
8
decarboxylative cascade
8
cascade cyclization
8
cyclization propargylic
8
propargylic cyclic
8
cyclic carbonates/carbamates
8
carbonates/carbamates pyridinium
8
pyridinium 14-zwitterionic
8
14-zwitterionic thiolates
8
fused polyheterocyclic
8

Similar Publications

Article Synopsis
  • The study presents a method using TMSOTf to create spiroketal derivatives through hydroalkoxylation and cycloaddition reactions involving hydroxy cyclopropenes and aldehydes.
  • This process generates a donor-acceptor cyclopropane intermediate, allowing for the efficient synthesis of [5.5]- and [6.5]-spiroketals.
  • The resulting spirocyclic compounds can be further modified to produce complex polycyclic heterocycles through metal halogen exchange and copper-catalyzed reactions, with a decarboxylation step that introduces a fourth chiral center.
View Article and Find Full Text PDF

Decarboxylative Aminomethylation of Indole-3-carboxylic Acids via Strain Release-Driven Ring Opening of 1,2-Oxazetidines.

Org Lett

October 2024

Department of Otolaryngology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan, Hubei 430071, China.

A copper-catalyzed decarboxylative aminomethylation of indole-3-carboxylic acids with 1,2-oxazetidines has been developed, enabling the rapid synthesis of structurally diverse 3-aminomethylindoles in good to excellent yields. Remarkably, an unprecedented decarboxylative aminomethylation/cyclization cascade was further achieved by a combination of copper and iron salts to construct complex γ-carbolines with high efficiency. It is worth noting that one of the obtained products proved to be a good dual-emissive luminogen, exhibiting both aggregation-caused quenching and aggregation-induced emission.

View Article and Find Full Text PDF

The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper-allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have been obtained.

View Article and Find Full Text PDF

Decarboxylative C(sp2)-heteroatom cross-coupling reactions hold extraordinary potential for the sustainable preparation of biologically active scaffolds. Herein, we report a copper sulfate/1,10-phenathroline catalytic system for the decarboxylative intramolecular C(sp2)-O, C(sp2)-S, and C(sp2)-N coupling reactions leading to the construction of a series of benzo[]furans, benzo[]thiophenes, and indole derivatives from the corresponding coumarins, thiocoumarins, or quinolones, respectively. Our mechanistic study based on benzo[]furan formation suggests a three-step process of the transformations, which consists of (i) base-mediated hydrolytic ring opening of coumarin, (ii) copper-oxygen co-initiated radical decarboxylation, and (iii) copper-catalyzed C-heteroatom cross coupling.

View Article and Find Full Text PDF

Decarboxylative Cyclization of Ethynyl Benzoxazinanones with Imidazolidines to Access 2,3-Indole-Fused 1,4-Diazocines.

Org Lett

June 2024

Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.

2,3-Indole-fused 1,4-diazocines represent a new family of indole alkaloid compounds and are difficult to access by the reported protocols. Herein, we report a copper-catalyzed decarboxylative cyclization of cyclic propargylic carbamates with imidazolidines via sequential C-N/C-N/C-C bond formation to deliver a series of 2,3-indole-fused 1,4-diazocines, with a broad substrate scope and mild conditions.

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!