Highly Diastereoselective Synthesis of Multifunctionalized Dihydrofurans by a K3PO4‐Promoted Michael Addition‐Alkylation Reaction DOI

Juhua Feng,

Jinxiang Feng,

Juanhong Li

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(37)

Published: Oct. 6, 2023

Abstract A simple and beneficial strategy for the construction of 2,3‐dihydrofurans from α‐bromochalcones α‐substituted cyanoketones via Michael addition‐alkylation reaction has been realized. This transformation was well compatible with various cyanoketones, corresponding multifunctionalized were obtained in up to 98 % yield. highly diastereoselective variant also developed. Moreover, could be performed on gram‐scale.

Language: Английский

Recent advances in the synthesis and applications of β-keto sulfones: new prospects for the synthesis of β-keto thiosulfones DOI
Raju Jannapu Reddy,

Arram Haritha Kumari,

Jangam Jagadesh Kumar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(14), P. 3087 - 3118

Published: Jan. 1, 2021

This review highlights recent developments relating to the preparation of β-keto sulfones and thiosulfones. And, also focused on widespread synthetic applications for assembling many valuable carbo- heterocycles.

Language: Английский

Citations

60

Metal-Free and Regioselective Synthesis of Functionalized α-Carbolines via [3 + 3] Annulation of Morita–Baylis–Hillman Acetates of Nitroalkenes with Iminoindolines DOI
Sudheesh T. Sivanandan, Irishi N. N. Namboothiri

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(12), P. 8465 - 8471

Published: May 28, 2021

A facile, metal-free method for the synthesis of substituted α-carbolines from secondary Morita–Baylis–Hillman (MBH) acetates nitroalkenes is presented. The cascade reaction MBH with tosyliminoindolines occurs regioselectively to form various a wide substrate scope. involves mild conditions, and products are formed in high yields within short time. amenability scale up synthetic applications have been demonstrated.

Language: Английский

Citations

25

Three-Component Sulfonylation and Heteroannulation Enabled by 3-Fold Defluorofunctionalization of Trifluoromethyl Enones DOI

Shu-Ji Gao,

Xueying Huang, M Kellis

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 23, 2025

Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones biocompatible sodium sulfinates has been developed for the modular synthesis densely functionalized furans with regio-defined C2,4-bissulfonyl C3-trifluoromethyl substitutions. This three-component method proceeds through sequential sulfonylation intramolecular O-cyclization, enabling assembly one furan ring, formation C-SO2/C–O bonds, cleavage three C(sp3)-F bonds one-pot manner under transition metal-free conditions. Moreover, obtained product can further react benzyne precursor to generate 1,4-epoxynaphthalene Diels–Alder cycloaddition. The is also distinguished by its broad substrate scope, excellent functional group tolerance, scalability.

Language: Английский

Citations

0

Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones DOI Creative Commons
Arianna Quintavalla, Ruben Veronesi, Davide Carboni

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(13), P. 3267 - 3282

Published: April 21, 2021

Abstract A synthetic procedure, catalysed by Ir(ppy) 3 under visible‐light irradiation, for the chemodivergent synthesis of 2,3‐dihydrofurans ( ) or β,γ‐unsaturated ketones 7 starting from α‐halo 1 and alkenes 2 has been developed. The mild reaction conditions redox‐neutral nature process make it particularly sustainable avoiding use both sacrificial reactants stoichiometric strong oxidants. Careful experimental investigations, supported DFT calculations, allowed to disclose in details a possible mechanistic pathway direct chemodivergently either toward , depending not only on substrates, but also choice conditions. magnified image

Language: Английский

Citations

18

Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes DOI
Sudheesh T. Sivanandan, Divya K. Nair, Irishi N. N. Namboothiri

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(31), P. 6243 - 6262

Published: Jan. 1, 2023

This article reviews the recent applications of Morita–Baylis–Hillman and Rauhut–Currier adducts nitroalkenes. It also covers mechanistic aspects, including key intermediates reaction pathways.

Language: Английский

Citations

7

The synthesis of O/S-heterocycles starting from β-nitrostyrenes: A recent update DOI
Chunmei Li, Kai Yin, Xiang Zhou

et al.

Tetrahedron, Journal Year: 2023, Volume and Issue: 149, P. 133717 - 133717

Published: Nov. 2, 2023

Language: Английский

Citations

7

Developments and applications of α-bromonitrostyrenes in organic syntheses DOI Creative Commons
Fatemeh Doraghi, Mohammad Mahdi Aghanour Ashtiani, Fatemeh Moradkhani

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(21), P. 14835 - 14846

Published: Jan. 1, 2024

In this work, we have described the use of α-bromonitrostyrenes in synthesis a wide variety carbocyclic and heterocyclic compounds under organocatalysis, metal catalysis, base-catalysis systems as well catalyst-free reactions.

Language: Английский

Citations

2

Bromonitroalkenes as efficient intermediates in organic synthesis DOI
Azim Ziyaei Halimehjani,

Hoonam Tahvildari

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(24), P. 4801 - 4838

Published: Jan. 1, 2024

Bromonitroalkenes are useful molecules in synthetic organic chemistry. They mainly prepared from nitroalkenes

Language: Английский

Citations

2

Formation of Five- and Six-membered Oxygen-containing Heterocycles on the Basis of 1-halo-1-nitroalkenes DOI
Kirill А. Gomonov, Ilya A. Pilipenko

Chemistry of Heterocyclic Compounds, Journal Year: 2023, Volume and Issue: 59(1-2), P. 1 - 4

Published: Feb. 1, 2023

Language: Английский

Citations

6

Synthesis of pyrrolidin-2-ylidenes and pyrrol-2-ylidenes via 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides to nitrostyrenes DOI
Issa Yavari,

Ramin Mohsenzadeh,

Parisa Ravaghi

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(25), P. 5265 - 5273

Published: Jan. 1, 2023

Diastereoselective formation of pyrrolidene-2-ylidenes by the Huisgen reaction hydrogen-bond-assisted azomethine ylides with β-bromo-β-nitrostyrenes is reported.

Language: Английский

Citations

5