Synthesis of Aryl‐(E)‐2‐(azidomethyl)alkenoate and Aryl‐(Z)‐2‐(azidomethyl)acrylonitrile from Aryl Aldehydes and Activated Alkenes via One‐Pot Way. (27th April 2016)

• Record Type: Journal Article
• Authors: Lee, Sang‐Jin; Yang, Hae‐Won; Han, Tae‐Hwi; Yoon, Cheol Min
• Is Part Of: Bulletin of the Korean Chemical Society. Volume 37:Number 5(2016)
• Page Start: 771
• Page End: 774
• Publication Date: 2016-04-27
• Subjects: Baylis–Hillman reaction -- One‐pot reaction -- Nucleophilic substitution -- Allyl azide -- Solvent‐free; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/bkcs.10751
• Languages: English
• ISSNs: 0253-2964

Abstract

Abstract : An efficient one‐pot preparation of aryl‐( E )‐2‐(azidomethyl)alkenoate and aryl‐( Z )‐2‐(azidomethyl)acrylonitrile from aryl aldehydes and activated alkenes (acrylate and acrylonitrile) were developed. The method consisted of a three‐step one‐pot process involving Baylis–Hillman reaction of aryl aldehydes and activated alkenes using DABCO followed by acetylation using acetic anhydride and a catalytic amount of DMAP, and nucleophilic substitution with sodium azide in DMF at room temperature.