Mechanistic Insights into the Palladium‐Catalyzed Domino Synthesis of 10,11‐Dihydro‐5H‐dibenzo[b,e][1,4]diazepines

Laha, Joydev K.; Tummalapalli, K. S. Satyanarayana; Gupta, Ankur

doi:10.1002/ejoc.201402207

Cited by 17 publications

(13 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a practical alternative to dibenzodiazepinone reduction, Laha and co-workers developed a Pd/ L6 -catalyzed tandem process for the synthesis of 10,11-dihydro-dibenzodiazepines ( 136 ) ( Scheme 24 a). 120 Presumably, intermolecular Pd-catalyzed N-benzylation of 1,2-diaminoarenes with 2-bromobenzyl bromides occurs first, followed by intramolecular N-arylation to furnish the seven-membered-ring-containing heterocycles in 23–91% yield. 121 Additionally, Domínguez and co-workers prepared a series of (pyrazolo)dibenzodiazepines ( 140 ) in an effort to enhance the drug-like properties of the final compounds ( Scheme 24 b).…”

Section: Anilinesmentioning

confidence: 99%

“…The Pd-catalyzed intramolecular coupling of anilines has also been used to prepare dibenzodiazepines, which are important pharmaceutical targets (Scheme ). As a practical alternative to dibenzodiazepinone reduction, Laha and co-workers developed a Pd/ L6 -catalyzed tandem process for the synthesis of 10,11-dihydro-dibenzodiazepines ( 136 ) (Scheme a) . Presumably, intermolecular Pd-catalyzed N-benzylation of 1,2-diaminoarenes with 2-bromobenzyl bromides occurs first, followed by intramolecular N-arylation to furnish the seven-membered-ring-containing heterocycles in 23–91% yield .…”

Section: Anilinesmentioning

confidence: 99%

See 1 more Smart Citation

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

View full text Add to dashboard Cite

Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

show abstract

Section: Anilinesmentioning

confidence: 99%

Section: Anilinesmentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

View full text Add to dashboard Cite

show abstract

“…[32] It should also be noted that we have had little success -despite numerous studies and efforts -to successfully achieve the same results using the structurally analogous, o-haloarylketimines. [34] In 2014, Laha et al [35] reported a palladium-catalyzed domino approach for the synthesis of a dihydro-DBDA class (10,11dihydro-5H-dibenzo[b,e][1,4]diazepines) starting from o-phenylenediamines and 2-bromobenzyl bromides or tosylates (Scheme 7). [34] In 2014, Laha et al [35] reported a palladium-catalyzed domino approach for the synthesis of a dihydro-DBDA class (10,11dihydro-5H-dibenzo[b,e][1,4]diazepines) starting from o-phenylenediamines and 2-bromobenzyl bromides or tosylates (Scheme 7).…”

Section: 4-dibenzodiazepinesmentioning

confidence: 99%

Metal‐Catalyzed Routes to Dibenzodiazepines (DBDAs) and Structural Analogues: Recent Advances

2018

View full text Add to dashboard Cite

It is common knowledge that the use of transition metals as catalysts has greatly revolutionized various coupling procedures to access heterocyclic compounds of significant industrial interest. Dibenzodiazepines (DBDAs) are a particularly important group of heterocyclic compounds, with considerable pharmaceutical applications. In this review, we look at some of the catalytic methods that have been developed during the last 10 years for the synthesis of these targets. Palladium catalysts have been frequently used for these transformations, and particularly for the Buchwald–Hartwig reaction which has been a key reaction in a number of synthetic pathways. Copper has also been frequently used, including some other metals like iron and molybdenum, but to a lesser extent. In most cases, the examples chosen are for the synthesis of DBDAs with interesting medicinal properties and will be of interest to medicinal chemists. It should also be mentioned that due to the structural characteristics of these compounds the potential for diversification – principally for functional group incorporation – is immense. Emerging and facilitating technologies have also been employed for the synthesis of these molecules and are reviewed here.

show abstract

mentioning

confidence: 99%

“…Very recently, we have developed an expedient domino synthesis of 10,11-dihydro-5H-dibenzo[b,e] [1,4]diazepines that are otherwise difficult to obtain by literature methods. 4 The methodology provided a workable access to various substituted 10,11-dihydro-5H-dibenzo[b,e] [1,4]diazepines for a general structure−activity relationship study. In this context, we had an opportunity to demonstrate the proof-of-concept on 10,11-dihydro-5H-dibenzo[b,e] [1,4]diazepines containing a cyclic secondary benzylamine moiety.…”

mentioning

confidence: 99%