Multigram-Scale Synthesis of a gem-Difluoro-Substituted 4,5,6,7-Tetrahydrobenzo[c]thiophen-4-one Heterocycle via Oxidative Chlorination and Radical Smiles Rearrangement DOI
Craig Jamieson, Martyn C. Henry,

Jack Q. Anderson

и другие.

Synlett, Год журнала: 2023, Номер unknown

Опубликована: Авг. 14, 2023

Abstract We report an optimized synthetic route towards a functionalized 4,5,6,7-tetrahydrobenzo[c]thiophene heterocycle bearing gem-difluoromethylene moiety in 4 steps with overall yield of 43%. The CF2 fragment was incorporated using building block approach, by coupling appropriate fluorinated alcohol C-3 sulfonyl chloride, synthesized via oxidative chlorination exocyclic benzyl thioether. Visible-light-mediated Smiles rearrangement the resulting fluorosulfonate ester then furnishes desired thiophene scaffold.

Язык: Английский

P(NMe2)3-Mediated Regioselective N-Alkylation of 2-Pyridones via Direct Deoxygenation of α-Keto Esters DOI
Nan Wang, Yuanyuan Huang, You Zi

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3657 - 3665

Опубликована: Фев. 17, 2024

A practical and regioselective direct N-alkylation of 2-pyridones is enabled by use α-keto esters in the P(NMe2)3-mediated deoxygenation process. The reaction proceeds under mild conditions to produce N-alkylated with high selectivity generality, protocol shown be applicable for scale-up synthesis, which makes it promising applications.

Язык: Английский

Процитировано

6

Advances in the Synthetic Utility of Difluorocarbene Generated from TMSCF3 (Ruppert‐Prakash Reagent) and Its Derivatives DOI Open Access
Jagadeesh Krishnan,

Kaja Sahib,

Keerthana G. Nair

и другие.

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Март 12, 2025

Abstract Organofluorine compounds are of pivotal significance particularly, in drug and agrochemical industries different strategies have been designed for their synthesis. The last two decades witnessed the emergence difluorocarbene as an efficient synthetic tool, providing easy access to organofluorine compounds. This review summarises reactions generated from Ruppert‐Prakash reagent (TMSCF 3 ) its derivatives TMSCF 2 Cl Br. Among various fluorination techniques available, chemistry offers a cost effective procedure, opening avenue large number details developments utility derivatives, till date.

Язык: Английский

Процитировано

0

Efficient Synthesis of O-Aryl Esters Using a Recyclable MWCNTs-MNPs/Met-NiCl2 Nanocatalyst in Ionic Liquid DOI
Réza Mohammadi, Suranjana V. Mayani,

Anjan Kumar

и другие.

Journal of Inorganic and Organometallic Polymers and Materials, Год журнала: 2025, Номер unknown

Опубликована: Май 19, 2025

Язык: Английский

Процитировано

0

2‐Hydroxypyridines as N‐ and O‐Nucleophiles in Organic Synthesis DOI
Shiwei Li, Gang Wang, Zhishi Ye

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(2)

Опубликована: Ноя. 6, 2023

Abstract 2‐Hydroxypyridines have emerged as versatile nucleophiles in organic synthesis. The N ‐ and O ‐functionalization of 2‐hydroxypyridines affords straightforward practical methods for the construction ‐substituted 2‐pyridones 2‐hydroxypyridines, which are important structural motifs numerous natural products, pharmaceuticals biologically active compounds. Nonetheless, competition between presents an inevitable formidable challenge. In past few decades, chemoselective and/or has received extensive attention from synthetic community, resulting development elegant effective strategies to address this chemoselectivity. This review provides a summary recent advancements realm transition‐metal organo‐catalyzed, well visible‐light promoted functionalization including ‐alkylation, ‐allylation, ‐arylation, ‐alkenylation, ‐alkenylation.

Язык: Английский

Процитировано

3

Gold(I)-catalyzed synthesis of N-alkenyl 2-pyridonyl sec-amines DOI
Ali Osman Karatavuk

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(27), С. 5646 - 5652

Опубликована: Янв. 1, 2024

One-pot gold( i )-catalyzed synthesis was developed in order to prepare N -alkenyl 2-pyridonyl amines. This method provides a series of amines moderate excellent yields (up 98%).

Язык: Английский

Процитировано

0

Multigram-Scale Synthesis of a gem-Difluoro-Substituted 4,5,6,7-Tetrahydrobenzo[c]thiophen-4-one Heterocycle via Oxidative Chlorination and Radical Smiles Rearrangement DOI
Craig Jamieson, Martyn C. Henry,

Jack Q. Anderson

и другие.

Synlett, Год журнала: 2023, Номер unknown

Опубликована: Авг. 14, 2023

Abstract We report an optimized synthetic route towards a functionalized 4,5,6,7-tetrahydrobenzo[c]thiophene heterocycle bearing gem-difluoromethylene moiety in 4 steps with overall yield of 43%. The CF2 fragment was incorporated using building block approach, by coupling appropriate fluorinated alcohol C-3 sulfonyl chloride, synthesized via oxidative chlorination exocyclic benzyl thioether. Visible-light-mediated Smiles rearrangement the resulting fluorosulfonate ester then furnishes desired thiophene scaffold.

Язык: Английский

Процитировано

0