Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

Tabassum, Rukhsana; Ashfaq, Muhammad; Oku, Hiroyuki

doi:10.1002/jhet.4193

Cited by 3 publications

(2 citation statements)

References 95 publications

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“…The catalytic effect of various catalysts has been screened, including pyridine-3-carboxylic acid (P3CA), pyridine- reported a multicomponent synthesis of 8-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives 257 using aldehyde 1, malononitrileand 2-aminophenol in presence of 30 mol% ammonium acetate in ethanol (Scheme 104). [123] The reaction pathway involves Knoevenagel condensation reaction, Michael addition, followed by rearrangement and cyclization. Dey et al utilized a novel bio-degradable heterogeneous catalyst, sulphonated rice husk (SRH), to synthesize the biologically active hexahydroquinoline derivatives 549 and hexahydroacridine-1,8-diones 550 in two different reaction conditions (Scheme 105).…”

Section: Synthesis Of Pyridines and Quinolinesmentioning

confidence: 99%

“…reported a multicomponent synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives 257 using aldehyde 1 , malononitrileand 2‐aminophenol in presence of 30 mol% ammonium acetate in ethanol (Scheme 104). [123] The reaction pathway involves Knoevenagel condensation reaction, Michael addition, followed by rearrangement and cyclization.…”

Section: Six‐membered Heterocyclic Compoundsmentioning

confidence: 99%

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Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Section: Synthesis Of Pyridines and Quinolinesmentioning

confidence: 99%

Section: Six‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

Tabassum

Ashfaq

Oku

2020

Journal of Heterocyclic Chem

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A one‐pot quick and efficient multicomponent reaction has been developed for the synthesis of a new series of functionalized 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives using 30 mol% ammonium acetate in ethanol as solvent. This economical protocol run smoothly to give variety of quinoline derivatives in 55% to 98% yield from inexpensive reagents and catalyst in mild reaction conditions. Various spectroscopic techniques like FTIR, 1 H NMR and 13 C NMR, MALDI‐TOF‐MS, and EI‐MS were used to study and confirm their structure.

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Investigation of the mechanism of [M–H]⁺ ion formation in photoionized N‐alkyl‐substituted thieno[3,4‐c]‐pyrrole‐4,6‐dione derivatives during higher order MSⁿ high‐resolution mass spectrometry

Sioud,

Amad,

Zhu

et al. 2024

Rapid Comm Mass Spectrometry

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RationaleThe mechanism underlying dopant‐assisted atmospheric pressure photoionization's (APPI) formation of ions is unclear and still under debate for many chemical classes. In this study, we reexamined the gas‐phase reaction mechanisms responsible for the generation of [M–H]+ precursor ions, resulting from the loss of a single hydrogen atom, in a series of N‐alkyl‐substituted thieno[3,4‐c]‐pyrrole‐4,6‐dione (TPD) derivatives.MethodsAtmospheric pressure photoionization combined with higher order MS/MSn using high‐resolution mass spectrometry (APPI‐HR‐CID‐MSn) and electronic structure calculations using density functional theory were used to determine the chemical structure of observed [M–H]+ ions.ResultsAs a result, the higher order MSn (n = 3) experiments revealed a reversed Diels–Alder fragmentation mechanism, leading to a common fragment ion at m/z 322 from the studied [M1–5–H]+ ion species. In addition, the calculation for two chemical structure models (N‐alkyl‐TPD1 and N‐alkyl‐TPD5) showed that the fragment structure, resulting from the removal of the hydrogen atom connected to the third carbon atom of the N‐alkyl side chain, has a more stable cyclic form compared with the linear one.ConclusionsThe proposed chemical structure of the N‐alkyl TPD ion species, following the loss of a single hydrogen atom, was revealed during APPI‐HR‐CID‐MSn (n = 3) experiments on the [M–H]+ species. Hydrogen radical (H•) abstraction from the alkyl side chain (e.g., hexyl, heptyl, octyl, 2‐ethylhexyl, and nonyl) triggered a rearrangement in the radical cation structure of the N‐alkyl‐TPD derivatives, initiating cyclization and forming a six‐membered ring that connects the oxygen atom to the third carbon atom in the alkyl chain. In addition, theoretical calculations supported the APPI‐HR‐CID‐MSn (n = 3) experiments by demonstrating that the proposed chemical structure, resulting from the intramolecular cyclization of the N‐alkyl‐TPD ion species, was stable in the presence of chlorobenzene. These findings will aid the structural determination and elucidation of molecules with similar core structures.

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Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

Cited by 3 publications

References 95 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

Investigation of the mechanism of [M–H]⁺ ion formation in photoionized N‐alkyl‐substituted thieno[3,4‐c]‐pyrrole‐4,6‐dione derivatives during higher order MSⁿ high‐resolution mass spectrometry

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Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

Cited by 3 publications

References 95 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

Investigation of the mechanism of [M–H]+ ion formation in photoionized N‐alkyl‐substituted thieno[3,4‐c]‐pyrrole‐4,6‐dione derivatives during higher order MSn high‐resolution mass spectrometry

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Investigation of the mechanism of [M–H]⁺ ion formation in photoionized N‐alkyl‐substituted thieno[3,4‐c]‐pyrrole‐4,6‐dione derivatives during higher order MSⁿ high‐resolution mass spectrometry