Pd-Catalyzed Tandem Cyclization via C–H Arylation and Acylation for the Construction of Polycyclic Scaffolds

Mu, Bing; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Chang, Junbiao; Wu, Yangjie

doi:10.1021/acs.orglett.6b02571

Cited by 35 publications

(13 citation statements)

References 54 publications

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“…Because the most active compound was the imidazopyridine 20c , we decided to add various substituents to the imidazopyridine moiety in order to evaluate which positions most affect activity. This was achieved from the corresponding commercially available substituted amino pyridines 21a – h , which were subjected to the previous cyclization-iodination sequence to provide 23a – h , − followed by Sonogashira cross-coupling to afford compounds 24a – h (Scheme , see Supporting Information for full details).…”

Section: Resultsmentioning

confidence: 99%

“…or I2, pyridine, 42% (19a) ; (c) Pd(PPh3)2Cl2 5%, CuI 10%, Et3N, THF, 50°C, 10-46 % Since the most active compound was the imidazopyridine 20c, we decided to add various substituents to the imidazopyridine moiety in order to evaluate which positions most affect activity. This was achieved from the corresponding commercially available substituted amino pyridines 21a-h which were subjected to the previous cyclization-iodination sequence to provide 23a-h 43,44,45,46,47,48,49 followed by Sonogashira cross-coupling to afford compounds 24a-h (Scheme 4, see Supplementary data for full details). Compound 29 (Scheme 5), bearing a 7-azaindole ring system was prepared by a sequence of transformations including iodination of the commercially available 7-azaindole with N-iodosuccinimide, protection with benzenesulfonyl chloride, Sonogashira reaction with the alkene 15a, and finally deprotection with TBAF in THF.…”

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confidence: 99%

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From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase

et al. 2021

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Significant inhibition of Aurora B was achieved by the synthesis of simplified fragments of benzosceptrins and oroidin belonging to the marine pyrrole-2-aminoimidazoles metabolites isolated from sponges. Evaluation of kinase inhibition enabled the discovery of a synthetically accessible rigid acetylenic structural analog EL-228 (1), whose structure could be optimized into the potent CJ2-150 (37. Here we present the synthesis of new inhibitors of Aurora B kinase which is an important target for cancer therapy through mitosis regulation. The biologically oriented synthesis yielded several nanomolar inhibitors. The optimized compound CJ2-150 (37) showed a non-ATP competitive allosteric mode of action in a mixed-type inhibition for Aurora B kinase. Molecular docking identified a probable binding mode in the allosteric site "F" and highlighted the key interactions with the protein. We describe the improvement of the inhibitory potency and specificity of the novel scaffold as well as the characterization of the mechanism of action.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase

et al. 2021

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“…In 2016 Mu and his co‐workers reported dehydrogenative cyclization of imidazo[1, 2‐ a ]pyridine with 2‐chlorobenzaldehyde derivatives through arylation and acylation using Pd catalyst (Scheme 16). [45] They had carried out the reaction in an aqueous medium with Xantphos ligand and tetra ‐butylammoniumbromide (NBu 4 Br) surfactant under air to form 6H‐benzo[b]imidazo‐[5, 1, 2‐de]quinolizin‐6‐one derivatives. Both electron‐donating or withdrawing groups containing imidazo[1, 2‐ a ]pyridines and 2‐chlorobenzaldehydes give good yields of the desired product.…”

Section: Functionalization Reactions Of Imidazo[1 2‐a]pyridinementioning

confidence: 99%

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Konwar

Bora

2021

ChemistrySelect

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Imidazo[1,2‐a]pyridine is an important nitrogen‐containing heterocycle from biological as well as pharmaceutical point of view. In recent years, regioselective functionalization of C−H bond of imidazo[1,2‐a]pyridine is extensively carried out using various transition metal‐based catalysts. Alkenylation, arylation, dual dehydrogenative annulations, formylation, thiolation, aminomethylation, dicarbonylation, phosphonylation along with other significant reactions are the progress in the field of functionalization of imidazopyridine. Most of these functionalizations are done at the C‐3 position of imidazo[1,2‐a]pyridine scaffold and in addition to that development towards C‐5 regioselectivity is also available. In this review, our aim is to present the recent advances for the functionalization of imidazo[1,2‐a]pyridine employing transition metal catalysts under significant reaction conditions.

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“…In the same year, Wu's research team described a direct route to 6H‐benzo[b]imidazo[5,1,2‐de]quinolizin‐6‐ones 32 by a Pd‐catalyzed cyclization of imidazo[1,2‐a]pyridines 30 with 2‐chlorobenzaldehydes 31 through a tandem C–H arylation and acylation reaction . The optimized condition for this reaction is the use of 5 mol% of Pd(OAc) 2 as a catalyst, 10 mol% of Xantphos as a ligand, 3.0 equiv.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Intramolecular cross‐dehydrogenative coupling of benzaldehyde derivatives: A novel and efficient route to benzocyclic ketones

Sheykhahmad

2019

J Chinese Chemical Soc

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Benzocyclic ketones are not only found throughout many natural products and synthetic pharmaceutically active compounds but also used as versatile building blocks in organic synthesis. In view of their importance, many researchers have been working to explore novel and efficient synthetic routes for this class of carbonyl compounds. Recently, cross-dehydrogenative coupling reactions have emerged as one of the most versatile and powerful synthetic strategies to construct various carbon-carbon and carbon-heteroatom bonds. In this regard, direct acylation of (hetero)arenes with aldehydes through C(sp 2 )-H activation opened up a new page on the synthesis of the titled compounds. In this focus-review, we discuss the most representative and important reports on the synthesis of cyclic diaryl ketones through intramolecular cross-dehydrogenative coupling reactions of corresponding benzaldehydes with emphasis on the mechanistic aspects of the reactions.

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Pd-Catalyzed Tandem Cyclization via C–H Arylation and Acylation for the Construction of Polycyclic Scaffolds

Cited by 35 publications

References 54 publications

From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase

From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

Intramolecular cross‐dehydrogenative coupling of benzaldehyde derivatives: A novel and efficient route to benzocyclic ketones

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