Transition Metal-Free Domino Hydroamination/Isomerization/Transamidation Sequence: An Entry to Trifluorinated γ-Lactams.

J Org Chem

Equipe Synthèse Organique et Phytochimie, Institut de Chimie, CNRS-UdS, UMR 7177, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg, France.

Published: August 2024


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

A method for the construction of trifluorinated-5-methylenepyrrolidinone is reported. This strategy combines an acid-catalyzed two-carbon homologation process between ynamides and aldehydes, providing CF-substituted dienes followed by a metal-free domino hydroamination/isomerization/transamidation sequence, delivering trifluorinated-5-methylenepyrrolidinone stereoselectively.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.4c00878DOI Listing

Publication Analysis

Top Keywords

metal-free domino
8
domino hydroamination/isomerization/transamidation
8
hydroamination/isomerization/transamidation sequence
8
transition metal-free
4
sequence entry
4
entry trifluorinated
4
trifluorinated γ-lactams
4
γ-lactams method
4
method construction
4
construction trifluorinated-5-methylenepyrrolidinone
4

Similar Publications

A facile one-step, three-component domino reaction has been established for the efficient synthesis of 3,5-disubstituted-2,6-dicyanoaniline derivatives, utilizing aldehydes in conjunction with aromatic, cyclic, and acyclic ketones, as well as malononitrile. This methodology employs CoCl·6HO as a catalyst specifically for aromatic and acyclic ketones, whereas a metal-free, base-catalyzed approach is applied for cyclic ketones. The reaction proceeds via a sequential mechanism that encompasses Knoevenagel condensation, Michael addition, and nucleophilic cyclization.

View Article and Find Full Text PDF

Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans.

J Org Chem

May 2025

Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China.

Herein, we developed an efficient nucleophile-controlled regiodivergent domino reaction between enetriones and γ-bromocrotonates. This method allowed for the rapid synthesis of a range of 1,3-dienic esters and tetrasubstituted pyrans under metal-free conditions. In the presence of pyridine, a S2 substitution/Michael addition/elimination sequence formed 1,3-dienic esters in satisfactory yields with high -stereoselectivities.

View Article and Find Full Text PDF

A novel method devoid of transition metal and azide is introduced for the synthesis of [1,2,3]triazolopyrido[3,4-b]indoles, [1,2,3]triazolo[1,5-a]pyridines, and [1,2,3]triazolo[1,5-a]quinoline, achieving good to excellent yields. This approach was suitable for a diverse array of N-heterocyclic starting substrates, including monocyclic (pyridine carbaldehyde), bicyclic (quinoline carbaldehyde), and tricyclic (β-carboline carbaldehyde or ketone). The current domino strategy involves the one-pot synthesis of 1- or 3-formyl-β-carbolines, pyridine carbaldehyde, or quinoline carbaldehyde with tosylhydrazine in the presence of CsCO, facilitating the creation of C-N and N-N bonds, as well as S-N cleavage.

View Article and Find Full Text PDF

Metal-Free Synthesis of Functionalized Indolizines via a Cascade Michael/S2/Aromatization Reaction of 2-Alkylazaarene Derivatives with Bromonitroolefins.

ACS Omega

December 2024

School of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang 550014, P. R. China.

A transition metal-free domino Michael/S2/aromatization annulation of 2-pyridylacetates with bromonitroolefins has been developed. A wide range of substrates containing various substituted groups was compatible with the present methodology and afforded functionalized indolizines with moderate to excellent yield (up to 99% yield). In addition, the potential practicality of the method stood out through scale-up reactions and further transformations to other valuable compounds.

View Article and Find Full Text PDF

A practically intriguing catalytic domino methodology has been developed for the synthesis of highly functionalized pyran and ethene-1,1,2-tricarbonitrile derivatives in a single-pot operation. The -dicyano olefins and the corresponding epoxide were taken as the reactive partners in the presence of a hydrogen bond donor (HBD)-catalyzed condition. The reaction was found to be highly efficient in terms of the formation of sequential C-C and O-C bonds along with an exceptional C-C coupling step through a metal-free organocatalytic pathway.

View Article and Find Full Text PDF