Palladium-catalyzed [5+2] oxidative annulation of N-Arylhydrazones with alkynes through C H activation to synthesize Benzo[d][1,2]diazepines

Asamdi, Manjoorahmed; Shaikh, Mohammedumar M.; Chauhan, Prakashsingh M.; Chikhalia, Kishor H.

doi:10.1016/j.tet.2018.05.051

Cited by 18 publications

(2 citation statements)

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“…Only when the aryl group (-Ar) was substituted with a -H, furnishing benzaldehyde as the starting material, the benzodiazepine was not obtained and the corresponding isoquinolone was isolated as the only product. A protocol to access benzo [2,3]diazepines 98 was developed through a Pd-catalyzed [5 + 2] annulation of N-arylhydrazones 96 with alkynes 97 (Scheme 47) [104]. Pd(OAc)2 was found to be optimal for the reaction conditions together with Cu(OAc)2 as the oxidant in 1,4-dioxane.…”

Section: 3-benzodiazepinesmentioning

confidence: 99%

“…The following coordination of the Pd complex with the alkyne allowed the insertion, providing the eight-membered palladacycle IV, from which the metal elimination and the formation of the C-N bond gave the benzodiazepine derivatives 98. A protocol to access benzo [2,3]diazepines 98 was developed through a Pd-catalyzed [5 + 2] annulation of N-arylhydrazones 96 with alkynes 97 (Scheme 47) [104]. Pd(OAc) 2 was found to be optimal for the reaction conditions together with Cu(OAc) 2 as the oxidant in 1,4-dioxane.…”

Section: 3-benzodiazepinesmentioning

confidence: 99%

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Palladium-Catalyzed Benzodiazepines Synthesis

2020

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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Section: 3-benzodiazepinesmentioning

confidence: 99%

Section: 3-benzodiazepinesmentioning

confidence: 99%