An improved synthesis of telmisartan <i>via</i> the copper-catalyzed cyclization of <i>o</i>-haloarylamidines

Zhang, Junchi; Li, Rui; Zhu, Fuqiang; Sun, Chang‐Liang; Shen, Jingshan

doi:10.1039/d0ra00886a

Cited by 9 publications

(10 citation statements)

References 36 publications

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“…S2 (5.34 g, 20 mmol) was reduced with Raney nickel (0.1 g) and hydrogen (5 bar) in ethanol (100 mL) 30 °C for 12 h. The insoluble substances were filtered away, and the filtrate was removed by a rotary evaporator to give 4 , (4.65 g, 98%) as a white solid; m.p. 148–150 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Generally, benzimidazole compounds were most often constructed by condensation of o -phenylenediamines with carboxylic acid derivatives − as well as aldehydes, − ketones, primary aliphatic amines, and alcohols , (Scheme A). Additionally, the synthesis of benzamidines from amidines through metal-catalyzed or oxidative cyclization was also explored (Scheme B). − Recently, benzimidazoles were generated from N -phenylamidoxime esters with the iridium photocatalyst 1,2,4-thiadiazole-5-thiones, 1,2,4-oxadiazole-5-(4 H )-thiones, and fulleroimidazole derivatives .…”

Section: Introductionmentioning

confidence: 99%

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Facile Synthesis of Benzimidazoles via N-Arylamidoxime Cyclization

et al. 2022

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A facile synthesis of benzimidazoles was described by a one-pot process containing acylation–cyclization of N-arylamidoxime. This method provided an alternative synthesis of benzimidazoles with a certain diversity of substituted groups in acceptable yields (up to 96%). More importantly, the construction of bis-benzimidazole (8), the key intermediate for making telmisartan, was achieved by adopting this method that enabled avoiding the undesired nitration with nitric/sulfuric acid and the cyclization in polyphosphoric acid in the existing operations.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Benzimidazoles via N-Arylamidoxime Cyclization

et al. 2022

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“…The total synthesis started from the commercially available 4-Nitro- m -toluic acid and it was achieved in seven steps with an overall yield of 54%. The advantage of this synthesis, relatively to the previous reported, is the absence of the use of possibly harmful HNO 3 /H 2 SO 4 for nitration and polyphosphoric acid (PPA) for cyclisation ( Scheme 11 , [ 40 ]).…”

Section: Synthetic Routes Of Different Sartansmentioning

confidence: 99%

“… Synthesis of telmisartan by Zhang, J et al The nitrile derivative 7 in the last step is converted to carboxylate analog 8 [ 40 ]. …”

Section: Figures and Schemesmentioning

confidence: 99%

Rational Design and Synthesis of AT1R Antagonists

et al. 2021

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Hypertension is one of the most common diseases nowadays and is still the major cause of premature death despite of the continuous discovery of novel therapeutics. The discovery of the Renin Angiotensin System (RAS) unveiled a path to develop efficient drugs to fruitfully combat hypertension. Several compounds that prevent the Angiotensin II hormone from binding and activating the AT1R, named sartans, have been developed. Herein, we report a comprehensive review of the synthetic paths followed for the development of different sartans since the discovery of the first sartan, Losartan.

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“…In 2020, Shen et al designed an efficient synthetic route for telmisartan. They focused their attention on the synthesis of the bis-benzimidazole intermediate 65 via Cu catalysis, avoiding PPA as a condensing agent ( Scheme 30 ) [ 80 ].…”

Section: Telmisartanmentioning

confidence: 99%

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

2021

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The outbreak of SARS-CoV-2 has drastically changed our everyday life and the life of scientists from all over the world. In the last year, the scientific community has faced this worldwide threat using any tool available in order to find an effective response. The recent formulation, production, and ongoing administration of vaccines represent a starting point in the battle against SARS-CoV-2, but they cannot be the only aid available. In this regard, the use of drugs capable to mitigate and fight the virus is a crucial aspect of the pharmacological strategy. Among the plethora of approved drugs, a consistent element is a heterocyclic framework inside its skeleton. Heterocycles have played a pivotal role for decades in the pharmaceutical industry due to their high bioactivity derived from anticancer, antiviral, and anti-inflammatory capabilities. In this context, the development of new performing and sustainable synthetic strategies to obtain heterocyclic molecules has become a key focus of scientists. In this review, we present the recent trends in metal-promoted heterocyclization, and we focus our attention on the construction of heterocycles associated with the skeleton of drugs targeting SARS-CoV-2 coronavirus.

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An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines

Abstract: A concise synthetic route of telmisartan was developed via the copper-catalyzed cyclization of o-haloarylamidines, avoiding the use of HNO3/H2SO4 and polyphosphoric acid (PPA).

Cited by 9 publications

References 36 publications

Facile Synthesis of Benzimidazoles via N-Arylamidoxime Cyclization

Facile Synthesis of Benzimidazoles via N-Arylamidoxime Cyclization

Rational Design and Synthesis of AT1R Antagonists

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

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