Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(9), P. 4607 - 4647

Published: Jan. 1, 2024

This review collectively discussed the utilisation of alcohols in various organic transformations and their application toward intermediates drugs, drug derivatives natural product-like molecules.

Language: Английский

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Designing Cobalt(II) Complexes for Tandem Dehydrogenative Synthesis of Quinoline and Quinazoline Derivatives

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 514 - 518

Published: Jan. 9, 2024

In this work, we have constructed three new Co(II) complexes in which steric features govern their structural geometry. The metal ligand-cooperation behavior of the alkoxy arm is utilized to explore catalytic activities these with respect dehydrogenation. A wide range C-3-substituted quinoline and quinazoline derivatives were synthesized high yields. developed protocol's usefulness enhanced by chemoselective transformation different fatty alcohols synthesize heterocycles having distal unsaturation. Various kinetic, mechanistic, control studies conducted comprehend reaction route.

Language: Английский

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Unlocking the photo-dehydrogenation ability of naphthalene monoimide towards the synthesis of quinazolinones

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(7), P. 2840 - 2845

Published: Jan. 1, 2023

A photocatalytic method involving naphthalene monoimide has been shown to synthesize quinazolinones under very mild reaction conditions.

Language: Английский

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Symmetrical Bis-Hydrazone Ligand-Based Binuclear Oxido/Dioxido-Vanadium(IV/V) Complexes: Synthesis, Reactivity, and Catalytic Applications for the Synthesis of Biologically Potent 2-Phenylquinazolin-4-(3H)-ones

Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 22, 2025

Symmetrical bis(hydrazone)-based ligands, H4dar(bhz)2 (I), H4dar(fah)2 (II), H4dar(nah)2 (III), and H4dar(inh)2 (IV) obtained from 4,6-diacetylresorcinol (H2dar) different hydrazides [benzoylhydrazide (Hbhz), isonicotinoylhydrazide (Hinh), nicotinoylhydrazide (Hnah), 2-furoylhydrazide (Hfah)], were used to prepare potassium salts of binuclear cis-[VVO2]+ complexes, {K(H2O)2}2[(VVO2)2dar(bhz)2] (1), {K(H2O)2}2[(VVO2)2dar(fah)2] (2), {K(H2O)2}2[(VVO2)2dar(nah)2] (3), {K(H2O)2}2[(VVO2)2dar(inh)2] (4), [VIVO]2+ [{VIVO(MeOH)}2dar(bhz)2] (5), [{VIVO(MeOH)}2dar(fah)2] (6), [{VIVO(MeOH)}2dar(nah)2] (7), [{VIVO(MeOH)}2dar(inh)2] (8). In the presence warm MeOH/DMSO (4:1), 3 changed {K(H2O)2}[(VVO2)2Hdar(nah)2]·DMSO (3a·DMSO). Single crystal XRD studies 1 3a confirm a structure along with distorted square pyramidal geometry each vanadium center where bis{ONO(2-)} ligands coordinate through phenolate-O, azomethine-N, enolate-O atoms unit. While growing crystals 6 in EtOH, part it oxidizes gives [{VVO(OEt)}2dar(fah)2] (9) powdery 6. Complex 9 has octahedral structure. These complexes as catalysts for synthesis biologically important 2-phenylquinazolin-4-(3H)-ones having aryl aldehydes, they all show excellent catalytic performance (up 97% yield) less reaction time low temperature, 70% aqueous TBHP/30% H2O2 greener oxidant. Generally, these perform better than their mononuclear analogues. Spectroscopy, DFT studies, isolated intermediates have helped proposing suitable mechanism reaction.

Language: Английский

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A Systematic Review of Synthetic and Anticancer and Antimicrobial Activity of Quinazoline/Quinazolin‐4‐one Analogues

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Abstract Quinazolines/quinazolin‐4‐ones are significant nitrogen‐containing heterocycles that exist in various natural products and synthetic scaffolds with diverse medicinal pharmacological applications. Researchers across the globe have explored numerous strategies to develop safer more potent quinazoline/quinazolinone analogues, particularly for combating cancer microbial infections. This review systematically examines scholarly efforts toward understanding this scaffold's pathways relevance, emphasizing role of metal non‐metal catalysts other reagents their synthesis. Additionally, article discusses selected compounds’ anticancer antimicrobial properties, a brief look into structure‐activity relationships.

Language: Английский

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Synthesis of Quinazolin-4(3H)-ones via a novel approach

Journal of Saudi Chemical Society, Journal Year: 2023, Volume and Issue: 27(2), P. 101597 - 101597

Published: Jan. 5, 2023

The present work was designed based on the new multi-component reaction, which forms 2-aryl/alkyl-quinazolin-4(3H)-ones in a one-pot reaction with good to excellent yields (86–97 %) using 2-aminobenzoic acid, organic and ammonium hexafluorophosphate (NH4PF6). advantages of presented method include inexpensive readily available starting materials, simple procedures, easy workup. In this newly discovered method, (NH4PF6) used as highly efficient reagent catalyst for quinazolin-4(3H)-ones synthesis. All synthesized compounds were characterized by 1H NMR 13C techniques.

Language: Английский

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Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2494 - 2504

Published: Feb. 7, 2024

We report the atom-economic and sustainable synthesis of biologically important 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide (DHBD) derivatives from readily available aromatic primary alcohols 2-aminobenzenesulfonamide catalyzed by nickel(II)-N∧N∧S pincer-type complexes. The synthesized nickel complexes have been well-studied elemental spectroscopic (FT-IR, NMR, HRMS) analyses. solid-state molecular structure complex 2 has authenticated a single-crystal X-ray diffraction study. Furthermore, series (24 examples) utilizing 3 mol % Ni(II) catalyst through acceptorless dehydrogenative coupling benzyl with benzenesulfonamide. Gratifyingly, catalytic protocol is highly selective yield up to 93% produces eco-friendly water/hydrogen gas as byproducts. control experiments plausible mechanistic investigations indicate that in situ generated aldehyde benzenesulfonamide leads desired product. In addition, large-scale one thiadiazine unveils synthetic usefulness current methodology.

Language: Английский

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Cobalt-Centered Supramolecular Nanoensemble for Regulated Aerobic Oxidation of Alcohols and “One-Pot” Synthesis of Quinazolin-4(3H)-ones

ACS Applied Materials & Interfaces, Journal Year: 2023, Volume and Issue: 15(42), P. 49246 - 49258

Published: Oct. 16, 2023

The supramolecular assemblies of the donor–acceptor (D–A) system Im-Tpy, having phenanthro[9,10-d]imidazole as donor and terpyridyl group acceptor unit, have been developed, which serve host to stabilize Co(II) in its nanoform. as-prepared nanoensemble Im-Tpy@Co DMSO:water (7:3) shows high thermal stability photostability. Even case solvent mismatch, i.e., on dilution with cosolvent THF/DMSO, insignificant changes were observed size/morphology nanoensemble. low catalytic loading (0.1 mol % Co) catalyzes oxidation a wide variety alcohols aromatic aldehydes/ketones using visible light radiations source energy without need any additive at room temperature. In comparison already reported systems, exhibits turnover numbers (TONs) frequencies (TOFs). practical application has also demonstrated gram-scale synthesis 4-chlorobenzaldehyde. recyclability up four cycles leaching morphological changes. present study demonstrates activity "one-pot" quinazolin-4(3H)-ones from 2-aminobenzamide primary better efficiency other transition-metal-based systems.

Language: Английский

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Dithionite-Mediated Tandem Nitro Reduction/Imine Formation/Intramolecular Cyclization for the Synthesis of Dihydro-benzothiadiazine-1,1-dioxides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 725 - 730

Published: Dec. 9, 2023

A one-pot, tandem reductive annulation of 2-nitrobenzenesulfonamides with aldehydes to the synthesis substituted 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides in presence sodium dithionite (Na2S2O4) is reported under mild conditions. The method involves situ reduction nitro group followed by condensation form an imine, which upon subsequent intramolecular cyclization forms product one-pot protocol features use inexpensive Na2S2O4 as exclusive reagent, appreciable functional tolerance, broad substrate scope, high yields, and scalability.

Language: Английский

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TBA(FeCl₃Br) Complex as a Photocatalyst in the C_sp3–H Bond Activation in Alcohols for the Synthesis of N-Based Heterocycles

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(27), P. 10276 - 10285

Published: June 25, 2024

The TBA(FeCl3Br) complex, formed in situ by the simple mixture of FeCl3 and tetrabutylammonium bromide (TBAB) MeCN, has been proven to be an outstanding photocatalyst promote selective oxidation alcohols aldehydes, under blue-light irradiation. Herein, we describe synthesis benzochalcogenazoles quinazolinones reaction with suitable ortho-substituted anilines mild conditions. Among green features, method reduces need derivatization circumventing use aldehydes as substrate allows isolation precipitation after washing crude ethyl ether, avoiding purification column chromatography.

Language: Английский

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