Visible‐Light‐Mediated Synthesis of 1‐Oxa‐4‐aza‐spiro Oxazolines by Spiroannulation of Quinones with Vinyl Azides. Issue 26 (13th July 2022)

• Record Type: Journal Article
• Authors: Sarkar, Subhankar; De, Aramita; Santra, Sougata; Khalymbadzha, Igor A.; Zyryanov, Grigory V.; Majee, Adinath
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 26(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-07-13
• Subjects: Photoredox catalyst -- Quinones -- Spirooxazolines -- Sustainable synthesis -- Vinyl azide -- Visible light; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200503
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A simple and efficient method has been developed to synthesize 1‐oxa‐4‐aza‐spirooxazolines. The reaction was carried out at room temperature using rose bengal as an organic photoredox catalyst and blue LED as a light source. It was observed that quinones underwent spiroannulation reaction with vinyl azide on C−O double bond instead of C−C double bond through which various corresponding 1‐oxa‐4‐aza‐spirooxazolines have been synthesized in good to excellent yields. Abstract : An unusual synthesis of 1‐oxa‐4‐aza‐spirooxazoline derivatives has been reported by the visible light‐mediated spiroannulation reaction of quinones with vinyl azides. A plausible mechanism was proposed based on some control experiments. Morpholine and indole‐substituted spiro‐products were also obtained as further functionalization of the main synthesized products.