Microwave-Assisted Copper-Powder-Catalyzed Coupling and Cyclization of β-Bromo-α,β-unsaturated Carboxylic Acids with 1,3-Diketones Leading to 2H-Pyran-2-ones

Ho, Son Long; Cho, Chan Sik; Sohn, Ho‐Sang

doi:10.1055/s-0034-1379103

Cited by 10 publications

(5 citation statements)

References 4 publications

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“…It is known that aryl and vinyl halides are coupled with 1,3‐dicarbonyl compounds in the presence of a copper or a palladium catalyst. [8d], , , Such a deacylative cyclocondensation is also exemplified by copper‐catalyzed cyclization reactions of aryl and vinyl halides with 1,3‐dicarbonyl compounds. [8d], , We confirmed that a similar treatment of 1a with 2a using MOF‐199, [Cu 3 (BTC) 2 (H 2 O) 3 ] n (BTC = benzene‐1,3,5‐tricarboxylate) in place of Fe 3 O 4 @SiO 2 @MOF‐199 under the conditions of entry 2 of Table afforded 3a in 74 % yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Binuclear Isoquinoline‐ and Pyridine‐Fused Benzimidazole‐4,7‐diones by Magnetic MOF‐199‐Catalyzed C–C Coupling/Cyclization Followed by Oxidation

2019

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2‐(2‐bromoaryl)‐4,7‐dimethoxy‐1H‐benzo[d]imidazoles and (Z)‐2‐(2‐bromovinyl)‐4,7‐dimethoxy‐1H‐benzo[d]imidazoles react with 1,3‐diketones by microwave irradiation in DMF in the presence of a catalytic amount of recyclable Fe3O4@SiO2@MOF‐199 along with a base to give binuclear isoquinoline‐ and pyridine‐fused benzimidazoles, respectively. Treatment of such binuclear N‐fused hybrid scaffolds with ceric ammonium nitrate in acetonitrile/H2O or HBr/FeCl3 in H2O affords binuclear isoquinoline‐ and pyridine‐fused benzimidazole‐4,7‐diones in good to high yields.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Binuclear Isoquinoline‐ and Pyridine‐Fused Benzimidazole‐4,7‐diones by Magnetic MOF‐199‐Catalyzed C–C Coupling/Cyclization Followed by Oxidation

2019

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“…recently reported on synthesis of indolo[1,2‐ c ]quinazolines from N‐{2‐[(2‐aminophenyl)ethynyl]phenyl}amides by ZnBr 2 ‐promoted domino hydroamination‐cyclization . During the course of our continuing studies directed towards cyclization reactions, we have identified several new synthetic methods for N‐fused hybrid scaffolds . Under these circumstances, this report describes copper‐catalyzed coupling and cyclization of 2‐(2‐bromophenyl)‐1 H ‐indoles with primary amides leading to indole‐fused quinazolines, indolo[1,2‐ c ]quinazolines.…”

Section: Methodsmentioning

confidence: 99%

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Yoo

Dao

Cho

2018

Bulletin Korean Chem Soc

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It is well-known that indole-fused quinazolines, indolo [1,2-c]quinazolines exhibit biological activities such as antibacterial and antifungal properties (Scheme 1). 1,2 Since the synthesis of indolo [1,2-c]quinazolines by thermal cyclization of 2-(2-aminophenyl)indoles with acyl cyanides followed by HCl treatment, many synthetic methods for such a hybrid scaffold are well documented. 3,4 Several groups have shown that indolo[1,2-c]quinazolines can be formed by condensation of 2-(2-aminophenyl)indoles with aromatic aldehydes and subsequent treatment with powdered KMnO 4 for oxidative cyclization. 1,2,5 Such a hybrid scaffold formation was also exemplified by palladium-catalyzed cyclocarbonylation of bis(o-trifluoroacetamidophenyl)acetylene with aryl or vinyl halides and triflates 6 and cyclization of 1-(N-arylimino)indoles formed by additionelimination between indoles and N-aryltrifluoroacetimidoyl chlorides. 7 It is also reported that 2-(2-halophenyl)indoles are coupled and cyclized with (aryl)methaneamines, amidine hydrochlorides, and amino acids in the presence of a copper catalyst to give indolo [1,2-c]quinazolines. 8-10 Wang et al. recently reported on synthesis of indolo[1,2-c]quinazolines from N-{2-[(2-aminophenyl)ethynyl]phenyl}amides by ZnBr 2 -promoted domino hydroamination-cyclization. 11During the course of our continuing studies directed towards cyclization reactions, 12 we have identified several new synthetic methods for N-fused hybrid scaffolds. 13 Under these circumstances, this report describes coppercatalyzed coupling and cyclization of 2-(2-bromophenyl)-1H-indoles with primary amides leading to indole-fused quinazolines, indolo[1,2-c]quinazolines.Treatment of 2-(2-bromophenyl)-1H-indole (1a) with an equimolar amount of formamide (2a) in DMF at 130 C for 24 h in the presence of a catalytic amount of CuI (10 mol %) along with Cs 2 CO 3 afforded indolo[1,2-c]quinazoline (3a) in 10% isolated yield with several unidentifiable products (Table 1, entry 1). Higher reaction rate and yield were observed with further addition of L-proline as a ligand (entry 2). It is known that the catalytic system of CuI combined with L-proline effectively catalyzes coupling and cyclization of 2-bromobenzamides with terminal alkynes leading to 3-alkylideneisoindolin-1-ones. 14 The molar ratio of [2a]/[1a] affected the yield of 3a and the yield increased with the increase of the molar ratio up to 2.0 along with complete conversion of 1a (entry 3). Lower reaction temperature resulted in a decreased yield of 3a (entry 4). The reaction proceeded using other amino acids such as glycine, L-phenylalanine, N,N-dimethylglycine, and 4-hydroxy-Lproline in place of L-proline, but the yield of 3a was generally lower than that by the use of L-proline except for 4-hydroxy-L-proline, which exhibited similar activity as Lproline (entries 5-8).Among bases examined under the employed conditions, Cs 2 CO 3 was shown to be the base of choice (entries 3 and 9-11). When used with L-proline and Cs 2 CO 3 , copper catalysts such as CuCl, CuBr...

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“…However, The conversion of the unsymmetrical 1,3‐diketone (1‐phenylbutane‐1,3‐dione) afforded a mixture of the corresponding products. The reaction pathway is expected to initially proceed between the coupling partners, leading to the formation of C−C cross‐coupled intermediate, which consecutively followed by deacylative cyclo‐condenzation to accomplish the product as shown in Scheme 2 [39] …”

Section: Formation Of Carbon‐carbon Bondmentioning

confidence: 99%

“…The reaction pathway is expected to initially proceed between the coupling partners, leading to the formation of CÀ C cross-coupled intermediate, which consecutively followed by deacylative cyclo-condenzation to accomplish the product as shown in Scheme 2. [39] Kifah S. M. Salih received his doctoral degree (2010) from the Technische Universität Kaiserslautern (Germany), where he worked with Prof. Dr. Lukas J. Gooßen on Ruthenium-catalyzed hydroamidation of terminal alkynes. He then took the opportunity to work with Prof. Dr. Werner R. Thiel (TU Kaiserslautern) as a research fellow, mainly focused on the synthesis of magnetic nanoparticles and their application in catalysis.…”

Section: Formation Of Carbon-carbon Bondmentioning

confidence: 99%

Modern Development in Copper‐ and Nickel‐Catalyzed Cross‐Coupling Reactions: Formation of Carbon‐Carbon and Carbon‐Heteroatom bonds under Microwave Irradiation Conditions

Salih

2022

Asian J Org Chem

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The use of transition metals in cross‐coupling reactions has been verified as a powerful tool in synthetic organic chemistry to access valuable pharmaceutical intermediates and functional organic molecules. Copper compounds were described for building a variety of Carbon‐Carbon and Carbon‐Heteroatom bonds more than a century ago. Whereas nickel‐catalyzed cross‐coupling was emerged in the 1972. The general reactivity of the reaction conversion was enhanced during the last two decades, particularly under microwave irradiation conditions. The focus of this review article accentuates the recent development and sustainable achievement of copper‐ and nickel‐catalyzed cross‐coupling of different electrophiles and nucleophiles or two sort of nucleophiles under microwave irradiation conditions. The published cross‐coupling protocols during the last ten years were critically reviewed, this includes the type and amount of metal catalyst used, solventless and ligandless conditions and the application in the synthesis of complex heterocycles. Furthermore, various proposed reaction mechanisms covering radical path or through the involvement of metal complexes in different oxidation states were highlighted and discussed.

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Microwave-Assisted Copper-Powder-Catalyzed Coupling and Cyclization of β-Bromo-α,β-unsaturated Carboxylic Acids with 1,3-Diketones Leading to 2H-Pyran-2-ones

Abstract: β-Bromo-α,β-unsaturated carboxylic acids were coupled and cyclized with 1,3-diketones by microwave irradiation in the presence of a catalytic amount of copper powder and base to give the corresponding 2H-pyran-2-ones in good to high yields.

Cited by 10 publications

References 4 publications

Synthesis of Binuclear Isoquinoline‐ and Pyridine‐Fused Benzimidazole‐4,7‐diones by Magnetic MOF‐199‐Catalyzed C–C Coupling/Cyclization Followed by Oxidation

Synthesis of Binuclear Isoquinoline‐ and Pyridine‐Fused Benzimidazole‐4,7‐diones by Magnetic MOF‐199‐Catalyzed C–C Coupling/Cyclization Followed by Oxidation

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Modern Development in Copper‐ and Nickel‐Catalyzed Cross‐Coupling Reactions: Formation of Carbon‐Carbon and Carbon‐Heteroatom bonds under Microwave Irradiation Conditions

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