Heteroarenobenzodiazepines. 4. 10-Piperazinyl-4H-thieno[3,2-b][1,5]- and -[3,4-b][1,5]benzodiazepines as potential neuroleptics

Chakrabarti, Jiban K.; Fairhurst, John; Gutteridge, N. J. A.; Horsman, Linda; Pullar, Ian A.; Smith, C.W.; Steggles, David J.; Tupper, David E.; Wright, Francesca

doi:10.1021/jm00182a014

Cited by 25 publications

(2 citation statements)

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“…Dibenzodiazepines are an important class of compounds in the pharmaceutical industry because of their potential use in the treatment of psychiatric disorders . An efficient, cost-effective, and high-yielding kilo-scale synthesis of 11-(piperazin-1-yl)-5 H -dibenzo[ b , e ][1,4]diazepine ( 34 ) featuring Cu-catalyzed coupling of 1-fluoro-2-nitrobenzene ( 31 ) and anthranilic acid ( 32 ) was reported by Wagh et al (Scheme ).…”

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.

154

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.

154

100

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“…Some of them are clozapine, olanzapine and flumezapine. In past years large number of derivatives from this class have been synthesized and tested for their pharmacological actions like muscarinic agonistic and dopamine antagonistic activities [1][2][3][4][5][6][7] . 11-(Piperazin-1-yl)-5H-dibenzo[b,e] [1,4]diazepine is a structural analogue of clozapine, an important atypical antipsychotic.…”

Section: Introductionmentioning

confidence: 99%