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Synthesis 2021; 53(16): 2828-2840
DOI: 10.1055/a-1490-1241
DOI: 10.1055/a-1490-1241
paper
Proton-Mediated Practical Synthesis of McGeachin-Type Bisaminals
This work was financially supported by the Beijing Natural Science Foundation (No. 2202041 to Z.Y.) and the Fundamental Research Funds for the Central Universities (No. XK1802-6 to Z.Y. and J.X.; No. 12060093063 to Z.Y.).
Abstract
A proton-mediated practical synthesis of McGeachin-type bisaminals from 2-(alkylamino)arenecarbaldehydes and primary amines is achieved, with trifluoroacetic acid as the proton donor. The use of a proton, a smallest electrophilic activator, allows previously inviable ortho-substituted anilines and linear and branched aliphatic amines to be viable substrates for McGeachin bisaminal synthesis. Overcoming the steric and electronic limitations provides a practical synthetic method. The applications in product derivation and pharmaceutical molecule modification are also demonstrated.
Key words
bisaminals - bridged azacycles - trifluoroacetic acid - proton - tandem reaction - iminodibenzodiazocineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1490-1241.
- Supporting Information
Publication History
Received: 26 March 2021
Accepted after revision: 23 April 2021
Accepted Manuscript online:
23 April 2021
Article published online:
19 May 2021
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