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Chemodivergent synthesis of functionalized methanodibenzo[b,f][1,5]diazocin-13-ylmethanones and tetrahydroquinolines via solvent-dependent AB2 and A2B2 multicomponent annulation reactions

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Abstract

A solvent-dependent chemodivergent approach was established for the synthesis of 6,12-methanodibenzo[b,f][1,5]diazocin-13-ylmethanones and 2,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines involving two distinct multicomponent processes under basic conditions. The AB2 three-component and A2B2 four-component reactions between 2-aminoarylaldehydes and aryl methyl ketones under basic conditions afforded 6,12-methanodibenzo[b,f][1,5]diazocin-13-ylmethanones (up to 95% yield) and trisubstituted tetrahydroquinolines (up to 84% yield), respectively, based on the nature of the solvent employed. The skeletal diversity and complexity were attained in these high atom- and step-economical processes by creating four new bonds in a single synthetic operation from readily available simple starting materials.

Graphical abstract: Chemodivergent synthesis of functionalized methanodibenzo[b,f][1,5]diazocin-13-ylmethanones and tetrahydroquinolines via solvent-dependent AB2 and A2B2 multicomponent annulation reactions

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Article information


Submitted
15 Apr 2020
Accepted
18 May 2020
First published
19 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Chemodivergent synthesis of functionalized methanodibenzo[b,f][1,5]diazocin-13-ylmethanones and tetrahydroquinolines via solvent-dependent AB2 and A2B2 multicomponent annulation reactions

I. Muthukrishnan, M. Karuppasamy, B. S. Vachan, D. Rajput, N. Subbiah, C. Uma Maheswari and V. Sridharan, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00449A

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