Synthesis of α-Chloroaldoxime <i>O</i>-Methanesulfonates and Their Use in the Synthesis of Functionalized Benzimidazoles

Yamamoto, Yuhei; Mizuno, Hiroo; Tsuritani, Takayuki; Mase, Toshiaki

doi:10.1021/jo8023544

Cited by 26 publications

(10 citation statements)

References 24 publications

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“…Benzimidazoles and 2‐aminobenzimidazoles are very powerful compounds because of their applications in therapeutic and biological sciences (Figure ) . These compounds were used as neuropeptide YY1 receptor antagonist, N ‐methyl‐D‐aspartate (NMDA) antagonist, factor Xa(FXa) inhibitor, poly(ADP‐ribose)polymerase (PARP) inhibitor and non‐peptide thrombin inhibitor .…”

Section: Figurementioning

confidence: 99%

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

2018

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The synthesis of aminobenzimidazoles has been demonstrated under mild reaction conditions using cobalt catalyst in one pot reaction. This methodology involved domino intra and intermolecular C-N cross-coupling reaction. In addition, functional group tolerance has been also explored.Benzimidazoles [1][2][3][4][5][6][7][8][9][10] and 2-aminobenzimidazoles [11][12][13][14][15][16][17][18][19][20][21] are very powerful compounds because of their applications in therapeutic [22][23] and biological sciences ( Figure 1). [24][25] These compounds were used as neuropeptide YY1 receptor antagonist, [26] N-methyl-D-aspartate (NMDA) antagonist, [27] factor Xa(FXa) inhibitor, [28] poly(ADP-ribose)polymerase (PARP) inhibitor [29] and non-peptide thrombin inhibitor. [30] In addition, these compounds show anti-inflammatory, antimicrobial and antibacterial activities. [31] Apart from that, these compounds can also be used for the synthesis of dyes and high-temperature resistance polymers. [32] Therefore, the construction of benzimidazole derivatives were developed by many researchers via both traditional methods [33][34][35] and C-N cross-coupling reactions using various transition metals such as Cu, [36][37][38][39][40] Pd, [41][42][43] Co, [44] Zn, [45][46][47] and Ru. [48] In this connection, we would like to demonstrate the methodology for the synthesis of benzimidazoles from thiourea in one pot reaction via desulphurization/substitution/domino C-N cross-coupling reaction using cobalt source as catalyst under mild reaction conditions.

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Section: Figurementioning

confidence: 99%

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

2018

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“… Their later report indicated that the cyclization was more conveniently carried out by a coupling reaction between an aniline and O -mesyl-α-chloroaldoxime 17 followed by annulation in the presence of N , N , N ′, N ′-tetramethylethylenediamine (TMEDA) in an one-pot reaction manner (eq 2 in Scheme ). In addition, the group established a convenient method to prepare substrate 17 by a sequence of N -chlorosuccinimide (NCS)-based α-chlorination of an aldoxime and a subsequent mesylation. By these methods, a variety of benzimidazoles 19 were prepared.…”

Section: Anilinesmentioning

confidence: 99%

Efficient Azacycle Formations Developed in Japanese Pharmaceutical Industries: Elegancy, Logistics, and Training (ELT) “Sandwich” for Process Chemists

Mizufune¹

2019

Org. Process Res. Dev.

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Efficient azacycle (nitrogen-containing heterocycle) formations developed by chemists in Japanese pharmaceutical industries have been selected from the published articles since the year 2000. The selected examples have been classified by the nitrogen source in the raw materials and have been reviewed from the following process chemistry perspectives; elegancy to establish the active pharmaceutical ingredient synthetic processes, logistics to procure/transform the required raw materials, and training for process chemists to consider azacycle formations according to a systematic approach. This mini-review also focuses on the molecular diversity created by the azacycle formations.

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“…The mixture was heated to reflux for 16 h, cooled to room temperature, and filtered through a pad of Celite which was washed well with ethyl acetate. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography (SiO 2 , 1:1, hexane/ethyl acetate) to provide 19 as an orange solid (81 mg, 39%): 31 2,6-Bis[(4R,5R)-4,5-Dihydro-4,5-diphenyl-1H-imidazol-2-yl]pyridine (20). Cesium carbonate (85 mg, 0.26 mmol), anhydrous toluene (1 mL), 2,6-dibromopyridine (47.4 mg, 0.2 mmol), tert-butyl isocyanide (68 μL, 0.6 mmol), (1R,2R)-(+)-1,2-diphenylethylenediamine (425 mg, 2.0 mmol), palladium(II) chloride (1.8 mg, 0.01 mmol), and dppp (8.2 mg, 0.02 mmol) were added to an oven-dried, three-necked flask under nitrogen.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed Multicomponent Synthesis of 2-Aryl-2-imidazolines from Aryl Halides and Diamines

2013

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Synthesis of α-Chloroaldoxime O-Methanesulfonates and Their Use in the Synthesis of Functionalized Benzimidazoles

Cited by 26 publications

References 24 publications

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

Efficient Azacycle Formations Developed in Japanese Pharmaceutical Industries: Elegancy, Logistics, and Training (ELT) “Sandwich” for Process Chemists

Palladium-Catalyzed Multicomponent Synthesis of 2-Aryl-2-imidazolines from Aryl Halides and Diamines

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