Stereoselective synthesis of (Z)-1, 3-bis(α, β-unsaturated carbonyl)-isoindolines from aldehydes and phenacyl azides under metal free conditions. Issue 75 (26th August 2021)

• Record Type: Journal Article
• Authors: Prasad, Budaganaboyina; Phanindrudu, Mandalaparthi; Nanubolu, Jagadeesh Babu; Kamal, Ahmed; Tiwari, Dharmendra Kumar
• Is Part Of: Chemical communications. Volume 57:Issue 75(2021)
• Page Start: 9542
• Page End: 9545
• Publication Date: 2021-08-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc02884g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We report herein our observation of an unprecedented stereoselective synthesis of 2 H -isoindolin-1, 3-ylidenes from 2-formylphenyl acrylates and phenacylazide in the presence of piperidine. Abstract : Here in the present manuscript, we report our observation of an unprecedented stereoselective synthesis of 2 H -isoindolin-1, 3-ylidenes from 2-(formylphenyl)acrylates and phenacylazide in the presence of piperidine. Unlike in our previous findings, in which we accessed 3-keto-isoquinolines from the same starting materials under slightly modified reaction conditions, this unexpected one-pot tandem reaction allows an efficient and simple method to access a variety of highly functionalized ethyl ( Z )-2-(( Z )-3-(2-oxo-2-arylethylidene)-2, 3-dihydro-1 H -benzo[ e ]isoindol-1-ylidene)-acetates in very good to excellent yields (up to 91%). The present methodology is compatible with a wide variety of functional groups.