Synthesis and Structure of Novel 4‐Arylamino‐2‐phenyl‐6‐substituted‐quinazoline

Zhang, Xing; Fu, Ying; Ye, Fei

doi:10.1002/jhet.905

Cited by 6 publications

(2 citation statements)

References 23 publications

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“…A comparison with the results obtained for these compounds employing our first-generation method revealed similar yields, although the previously mentioned advantages associated to the avoidance of phenol are noteworthy. A considerable improvement of the yield of the imidazolyl derivative 34 was observed in comparison with our previous method, and comparison with previous literature methods revealed our protocol to give improved yields in the cases when a comparison was possible, [26] avoiding the use of phenol or bulky phosphonium ligands. [27] In order to confirm the generality of our new protocol, we briefly examined the reactivity towards amines of several additional halogenated nitrogen heterocycles, including 2-chloroquinaxoline, [28] 4-chloroA C H T U N G T R E N N U N G purine, [29] 2-chlorobenzimidazole [11b, 30] and 2-chloropyridine [12f] to provide compounds 39-53 in excellent yields (Figure 7) for which no general method of synthesis was available.…”

Section: Resultsmentioning

confidence: 60%

Lewis Acid‐Catalyzed Generation of CC and CN Bonds on π‐Deficient Heterocyclic Substrates

2014

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Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic C À C and C À N bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on p-deficient heterocyclic substrates.

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Section: Resultsmentioning

confidence: 60%

Lewis Acid‐Catalyzed Generation of CC and CN Bonds on π‐Deficient Heterocyclic Substrates

2014

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“…A comparison with the results obtained for these compounds employing our first‐generation method revealed similar yields, although the previously mentioned advantages associated to the avoidance of phenol are noteworthy. A considerable improvement of the yield of the imidazolyl derivative 34 was observed in comparison with our previous method, and comparison with previous literature methods revealed our protocol to give improved yields in the cases when a comparison was possible,26 avoiding the use of phenol or bulky phosphonium ligands 27…”

Section: Resultsmentioning

confidence: 60%

Supramolekulare Polymere — Künftige Supertalente unter den Materialien

2015

Nachr Chem

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Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic CC and CN bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work‐up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π‐deficient heterocyclic substrates.

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The Core‐Shell Magnetic Mesoporous Microspheres Immobilized NHC‐Palladacycles: An Efficient and Recyclable Catalyst for Suzuki‐Miyaura Cross‐Coupling of Pharmaceutical Synthesis

Zuo

Zheng

et al. 2022

Asian J Org Chem

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The core-shell magnetic mesoporous microspheres immobilized NHC-palladacycles (NHC = N-heterocyclic carbene) catalyst with constrained aliphatic linker group (Fe 3 O 4 @mSiO 2 @NHCÀ Pd) were readily prepared by the welldesigned method, which showed higher palladium loading (0.20 mmol g À 1 ) and higher catalytic activity than the nonmesoporous catalysts (Fe 3 O 4 @SiO 2 @NHCÀ Pd) prepared by the same process in the Suzuki-Miyaura cross-coupling reactions of aryl chlorides and aryl boronic acids. Herein, Fe 3 O 4 @mSiO 2 @NHCÀ Pd could be used 12 times without significant activity loss, and no palladium leakage was detected in both the product and catalytic residue, highlighting the efficiency of our strategy for immobilizing the catalyst. Remarkably, this approach allows the synthesis of important drug intermediates 2-aryl-4-aminoquinazolines and o-tolylbenzonitrile (OTBN).

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Synthesis and Structure of Novel 4‐Arylamino‐2‐phenyl‐6‐substituted‐quinazoline

Cited by 6 publications

References 23 publications

Lewis Acid‐Catalyzed Generation of CC and CN Bonds on π‐Deficient Heterocyclic Substrates

Lewis Acid‐Catalyzed Generation of CC and CN Bonds on π‐Deficient Heterocyclic Substrates

Supramolekulare Polymere — Künftige Supertalente unter den Materialien

The Core‐Shell Magnetic Mesoporous Microspheres Immobilized NHC‐Palladacycles: An Efficient and Recyclable Catalyst for Suzuki‐Miyaura Cross‐Coupling of Pharmaceutical Synthesis

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