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

Isravel Muthukrishnan; Muthu Karuppasamy; B. S. Vachan; Diksha Rajput; Nagarajan Subbiah; C. Uma Maheswari; Vellaisamy Sridharan

doi:10.1039/D0QO00449A

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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†

Isravel Muthukrishnan,^a Muthu Karuppasamy,^a B. S. Vachan,^a Diksha Rajput,^b Nagarajan Subbiah,

^c C. Uma Maheswari

^a and Vellaisamy Sridharan

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur-613401, Tamil Nadu, India

^b Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu-181143, J&K, India
E-mail: vesridharan@gmail.com, sridharan.che@cujammu.ac.in

^c Department of Chemistry, National Institute of Technology, Warangal, Warangal-506004, Telangana, India

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.

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DOI: https://doi.org/10.1039/D0QO00449A
Article type: Research Article
Submitted: 15 Apr 2020
Accepted: 18 May 2020
First published: 19 May 2020

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Org. Chem. Front., 2020,7, 1616-1625

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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

I. Muthukrishnan, M. Karuppasamy, B. S. Vachan, D. Rajput, N. Subbiah, C. Uma Maheswari and V. Sridharan, Org. Chem. Front., 2020, 7, 1616 DOI: 10.1039/D0QO00449A

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