Diastereoselective synthesis of functionalized tetrahydropyridazines containing indole scaffolds via an inverse-electron-demand aza-Diels–Alder reaction. Issue 16 (18th June 2021)

• Record Type: Journal Article
• Authors: Chen, Taotao; Che, Chao; Guo, Zhefei; Dong, Xiu-Qin; Wang, Chun-Jiang
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 16(2021)
• Page Start: 4392
• Page End: 4398
• Publication Date: 2021-06-18
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00623a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A base-promoted and catalyst-free unprecedented inverse-electron-demand aza-Diels–Alder reaction between the in situ generated azoalkenes and 3-vinylindoles has been developed to afford tetrahydropyridazines containing indole scaffolds. 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 )- i Pr-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.