Issue 16, 2021

Diastereoselective synthesis of functionalized tetrahydropyridazines containing indole scaffolds via an inverse-electron-demand aza-Diels–Alder reaction

Abstract

An unprecedented base-promoted and catalyst-free inverse-electron-demand aza-Diels–Alder (IEDDA) reaction between easily available in situ generated azoalkenes and 3-vinylindoles has been developed. This efficient protocol afforded structurally important tetrahydropyridazines containing indole scaffolds with excellent results (72%–89% yields, >20 : 1 dr). Moreover, the catalytic asymmetric version of this reaction was preliminarily realized through a Cu/(S,S)-iPr-box system to prepare the desired chiral product with 81% yield and >20 : 1 dr and 93% ee. The cyclization products could also be well functionalized to access other useful organic molecules through simple transformations.

Graphical abstract: Diastereoselective synthesis of functionalized tetrahydropyridazines containing indole scaffolds via an inverse-electron-demand aza-Diels–Alder reaction

Supplementary files

Article information

Article type
Research Article
Submitted
21 apr 2021
Accepted
07 iyn 2021
First published
08 iyn 2021

Org. Chem. Front., 2021,8, 4392-4398

Diastereoselective synthesis of functionalized tetrahydropyridazines containing indole scaffolds via an inverse-electron-demand aza-Diels–Alder reaction

T. Chen, C. Che, Z. Guo, X. Dong and C. Wang, Org. Chem. Front., 2021, 8, 4392 DOI: 10.1039/D1QO00623A

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