ChemInform Abstract: Practical Asymmetric Synthesis of (S)‐MA20565, a Wide‐Spectrum Agricultural Fungicide.

Tanaka, Ken; Katsurada, Manabu; Ohno, F.; Shiga, Yasushi; Oda, Masaaki; Miyagi, Miwa; Takehara, Jun; Okano, Kazuya

doi:10.1002/chin.200018164

Cited by 2 publications

(2 citation statements)

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“…145 The synthesis of 156 via Cu-catalyzed coupling of diazonium salt 154 and acetaldoxime was also utilized in a practical asymmetric synthesis of a structurally similar candidate (S)-MA20565 (158) developed by Tanaka et al at Mitsubishi Chemical. 146 Compound 162 was developed as an antagonist for transient receptor potential cation channel subfamily V member 1 (TRPV1) for treatment of pain. [prepared through iodination of commercially available 159 with N-iodosuccinimide (NIS)] with a stoichiometric amount of CuCN in DMF at 120 °C (Scheme 42).…”

Section: Applications In Route Design Process Development and Scale-u...mentioning

confidence: 99%

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Yang

Zhao

2022

Org. Process Res. Dev.

153

100

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Cu-mediated Ullmann-type cross-coupling has experienced significant advances over the last century since the seminal publication by Ullmann in 1901. These advances have significantly expanded the scope of the original classical Ullmann coupling of aryl halides for formation of diaryl compounds to include the formation of carbon−heteroatom and other carbon− carbon bonds. The introduction of bidentate ligands drastically improved the performance of this class of transformations to enable milder reaction conditions that can tolerate a wide range of sensitive functional groups. Recent development of more powerful second-generation bidentate ligands has further allowed the coupling of less reactive aryl chlorides to proceed smoothly and realized low catalyst and ligand loadings for a broad scope of Ullmann-type cross-coupling reactions. As a result of these breakthrough advances in the past decades, Cu-mediated Ullmann-type cross-coupling reactions have been frequently implemented in academic research and have found ubiquitous industrial applications including the preparation of pharmaceutical and agrochemical products. This review provides an overview of selected general Cu-mediated Ullmann-type transformations for the formation of carbon− carbon and carbon−heteroatom (C−N, C−O, C−S, and C−P) bonds and their applications in route design, process development, and scale-up of pharmaceutical and agrochemical processes.

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Section: Applications In Route Design Process Development and Scale-u...mentioning

confidence: 99%

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Yang

Zhao

2022

Org. Process Res. Dev.

153

100

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“…Further finetuning of the substitution pattern of the newly installed benzyl group delivered compound 18 with a lower IC 50 value than rac-fenamidone (15) (Scheme 5). 29 Further successful examples of oxime reversal have been reported for strobilurin fungicides 30 and oxazoline acaricides. 31…”

Section: Reversal Of the Oxime Functionmentioning

confidence: 99%

Reversal of Functional Groups as a Useful Scaffold Hopping Tool in Agrochemistry

Lamberth

2022

J. Agric. Food Chem.

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Reverting the orientation of a functional group by exchanging molecular parts of it is an important scaffold hopping manipulation, as biologically active compounds and their analogs, which underwent such a transformation, are often similar in shape and physicochemical properties and therefore likely in their potency as well. This review will demonstrate, how the inversion of carboxamides, sulfonamides, carbamates, oximes, hydrazones, O,S-acetals, and ethers led to the discovery of highly active agrochemicals.

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ChemInform Abstract: Practical Asymmetric Synthesis of (S)‐MA20565, a Wide‐Spectrum Agricultural Fungicide.

Cited by 2 publications

References 1 publication

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Reversal of Functional Groups as a Useful Scaffold Hopping Tool in Agrochemistry

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