Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides

Zhang, Shi Qi; Cui, Yao; Guo, Bin; Young, David J.; Xu, Zhihong; Li, Hong Xi

doi:10.1016/j.tet.2020.131825

Cited by 14 publications

(9 citation statements)

References 64 publications

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“…Reaction of (2-aminophenyl)methanols 20 with benzamides 24 in the presence of FeCl 2 ·4H 2 O, phenanthroline (ligand) in CsOH·H 2 O, and toluene at 130°C for 24 h delivered quinazolines 39 in 43%–92% yields ( Scheme 13 ). ( Zhang et al, 2021 ) A broad substrate scope and hydrogen and water as the only byproducts of the reaction are the merits of this approach. The proposed mechanism involves the one-pot dehydrogenation of (2-aminophenyl)methanol 20 into aldehyde A, followed by condensation with benzamide 24 in the presence of a base to produce quinazoline 39 ( Scheme 5A ).…”

Section: First-row Transition Metal Catalystsmentioning

confidence: 99%

Transition-metal-catalyzed synthesis of quinazolines: A review

2023

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Quinazolines are a class of nitrogen-containing heterocyclic compounds with broad-spectrum of pharmacological activities. Transition-metal-catalyzed reactions have emerged as reliable and indispensable tools for the synthesis of pharmaceuticals. These reactions provide new entries into pharmaceutical ingredients of continuously increasing complexity, and catalysis with these metals has streamlined the synthesis of several marketed drugs. The last few decades have witnessed a tremendous outburst of transition-metal-catalyzed reactions for the construction of quinazoline scaffolds. In this review, the progress achieved in the synthesis of quinazolines under transition metal-catalyzed conditions are summarized and reports from 2010 to date are covered. This is presented along with the mechanistic insights of each representative methodology. The advantages, limitations, and future perspectives of synthesis of quinazolines through such reactions are also discussed.

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Section: First-row Transition Metal Catalystsmentioning

confidence: 99%

Transition-metal-catalyzed synthesis of quinazolines: A review

2023

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“…In addition, the cheap metal such as Fe was also served as catalyst for the ADC reaction to construct quinazolines. 21 Nevertheless, due to the harsh reaction conditions (such as the reaction temperature was up to 130 °C) and the need of high efficiency catalytic system to meet with the sustainable development, there is still room for improvement in the ADC reaction. Recently, we have developed a series of transfer hydrogenation and borrowing hydrogenation transformation via iridium catalysts.…”

Section: Figure 1 Selected Examples Of Pharmaceutically Active Compou...mentioning

confidence: 99%

Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines

Shui¹,

Zhong²,

Ouyang³

et al. 2022

Synthesis

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An efficient iridium-catalyzed acceptorless dehydrogenative coupling (ADC) reaction for the preparation of various quinazolines from 2-aminoarylmethanols and amides or nitriles had been developed. A wide range of substituted 2-aminobenzyl alcohols and (hetero)aryl or alkyl benzamides and nitriles were well compatible to afford various quinazolines in excellent yields. This new strategy merits the high atom-economy, mild reaction condition, simple operation and suited to a variety of substrates.

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“…A huge number of methods were described for the synthesis of quinazolines . However, they are notwithstanding due to the requirement of strong oxidizing agents, inert atmospheric conditions, high catalyst loadings, higher reaction temperatures, and relatively unstable aldehydes.…”

Section: Introductionmentioning

confidence: 99%

“…Fe-, Mn-, Ni-, Ru-, Ir-based metal complexes were also reported as catalysts in acceptorless dehydrogenative coupling for the synthesis of quinazoline using 2-aminobenzyl alcohol/amine with benzamides, ketones, (hetero)aryl or alkyl nitriles, aldehyde, alcohol, and benzylamines as stable starting materials however with high catalyst loading . Exceptionally, a Pd-catalyzed reaction for quinazolines from the reaction of primary alcohols with 2-aminobenzylamine was demonstrated by Kimura et al However, these methods involve simple dehydrogenative oxidation reactions with a limited substrate scope (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

NNO Pincer Ligand-Supported Palladium(II) Complexes: Direct Synthesis of Quinazolines via Acceptorless Double Dehydrogenative Coupling of Alcohols

2022

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A sustainable approach for the synthesis of substituted quinazolines by sequential acceptorless dehydrogenative coupling of 2-aminobenzyl alcohol with alcohols using new Pd(II)-NNO pincer-type complexes as catalysts was reported. Airstable palladium(II) complexes with general formula [Pd(L)-(PPh 3 )] (where L = 4-substituted methyl-2-pyrrolyl benzhydrazone ligands) were synthesized, and their compositions were recognized by analytical and spectral methods (Fourier transform infrared (FT-IR), NMR, and high-resolution mass spectrometry (HRMS)). Single-crystal X-ray crystallography confirmed the tridentate coordination of the ligands and the existence of square-planar geometry around the metal ion. A wide range of substituted quinazoline derivatives was synthesized from double dehydrogenation of benzyl alcohols using 1.5 mol % catalyst loading with a maximum of 93% yield. The formation of aminobenzaldehyde and benzaldehyde intermediates via a double dehydrogenative coupling reaction was confirmed by control experiments.

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Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides

Cited by 14 publications

References 64 publications

Transition-metal-catalyzed synthesis of quinazolines: A review

Transition-metal-catalyzed synthesis of quinazolines: A review

Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines

NNO Pincer Ligand-Supported Palladium(II) Complexes: Direct Synthesis of Quinazolines via Acceptorless Double Dehydrogenative Coupling of Alcohols

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