Diversity of Lawesson's Reagent: Advances and Scope

Asian Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 9(4), P. 508 - 528

Published: Jan. 27, 2020

Abstract Lawesson's reagent is a classic example of compound having remarkable construction and also distinctive chemical behaviour that can challenge stereotype conceptual explanations. At the very beginning, it was mainly known for its use in thionation various types carbonyl groups. However, over last few years chemists reported some appealing examples which nurture chemistry community to perceive innovative ideas. These include valuable heterocycles, important coupling reactions, decoration metal‐based attractive cores. Several reports provided comprehensive theoretical studies regarding mechanistic classification. This article gives an overview recent insights synthetic applications this famous from 2013 2019.

Language: Английский

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Recent developments by zinc based reagents/catalysts promoted organic transformations

Tetrahedron, Journal Year: 2021, Volume and Issue: 105, P. 132580 - 132580

Published: Nov. 24, 2021

Language: Английский

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A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(9), P. 2529 - 2541

Published: Jan. 1, 2019

A new robust method for the synthesis of 2,4,5-trisubstituted pyridines with high efficiency and broad functional group tolerance is described.

Language: Английский

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Synthesis of 1-Azaspiro[4.5]deca-1,3-dienes from N-Propargylic β-Enaminones in Basic Medium

Synthesis, Journal Year: 2019, Volume and Issue: 51(10), P. 2157 - 2170

Published: Feb. 18, 2019

A facile, efficient and unprecedented method for the synthesis of spiro-2H-pyrroles is reported. When reacted with 1-ethynylcyclohexylamine, α,β-alkynic ketones produced cyclohexane-embedded N-propargylic β-enaminones, which in presence cesium carbonate underwent nucleophilic cyclization to afford 1-azaspiro[4.5]deca-1,3-diene derivatives good excellent yields. This was found be general a variety β-enaminones demonstrated tolerance broad range aliphatic, aromatic heteroaromatic groups electron-withdrawing electron-donating substituents. The decoration pyrrole compounds spiro framework may exhibit potential molecules pharmacological interest.

Language: Английский

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Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(5), P. 3242 - 3253

Published: Jan. 20, 2022

The transformation of 2-imidazolines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines has been realized. A pseudo-three-component reaction with terminal electron-deficient alkynes (2 equiv) first generates imidazolidines, containing an N-vinylpropargylamine fragment. latter can then undergo a base-catalyzed domino aza-Claisen rearrangement/cyclization sequence, simultaneously constructing pyrrole and pyrazine rings. process works in broad substrate scope, delivering pyrrolo[1,2-a]pyrazines good to excellent yields (45–90%). This two-step approach be carried out one-pot fashion without noticeable decrease yield. Remarkably, three-component protocol for the introduction two different also developed.

Language: Английский

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A facile synthesis of 6-chloro-2-methylene-2,3-dihydro-1,4-oxazepines from N-propargylic β-enaminones

Tetrahedron, Journal Year: 2020, Volume and Issue: 76(48), P. 131650 - 131650

Published: Oct. 16, 2020

Language: Английский

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A New Strategy for the Synthesis of 4‐Propargyl‐Substituted 1H‐Pyrroles from N‐(5‐phenyl‐2,4‐pentadiynyl) β‐Enaminones

ChemistrySelect, Journal Year: 2019, Volume and Issue: 4(37), P. 11043 - 11047

Published: Oct. 1, 2019

Abstract A new method for the synthesis of 4‐propargyl‐substituted 1 H ‐pyrroles is described. When treated with sodium hydride in refluxing dichloromethane, N ‐(5‐phenyl‐2,4‐pentadiynyl) β‐enaminones, synthesized by coupling ‐propargylic β‐enaminones phenylacetylene, afforded pyrrole derivatives. This conversion was general a variety and displayed broad functional group tolerance. During reaction, not only cyclization linear precursors to ring takes place, but also propargyl introduced core one‐pot. The enrichment compounds unit might exhibit potential heterocyclic molecules pharmacological interest.

Language: Английский

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Synthesis, optical studies and DFT analysis of benzo[b][1,4]oxazepines and thiazepines: A promising fluorescent probe for sensing of picric acid

Materials Today Communications, Journal Year: 2023, Volume and Issue: 35, P. 106206 - 106206

Published: May 15, 2023

Language: Английский

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A facile one-pot synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines

Synthetic Communications, Journal Year: 2020, Volume and Issue: 51(5), P. 709 - 719

Published: Nov. 26, 2020

An unprecedented method for the synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines from N-(2,4-pentadiynyl) β-enaminones is reported. Upon treatment with Lawesson's reagent, were thionated to furnish β-enaminothiones, which immediately underwent 7-exo-dig cyclization generate in one-pot. A general trend was observed various and proceeded broad functional group tolerance. This operationally easy may provide quick access a library functionalized 1,4-thiazepines field pharmaceutical chemistry.

Language: Английский

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Synthesis of naturally occurring seven-membered nitrogen heterocycles and related bioactive compounds

Studies in natural products chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 189 - 235

Published: Jan. 1, 2023

Language: Английский

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