Synthesis of tetrahydrochromenes and dihydronaphthofurans via a cascade process of [3 + 3] and [3 + 2] annulation reactions: mechanistic insight for 6-endo-trig and 5-exo-trig cyclisation. Issue 9 (16th February 2023)

• Record Type: Journal Article
• Authors: Reddy, Yeruva Pavankumar; Srinivasadesikan, V.; Balamurugan, Rengarajan; Lin, M. C.; Anwar, Shaik
• Is Part Of: RSC advances. Volume 13:Issue 9(2023)
• Page Start: 5796
• Page End: 5803
• Publication Date: 2023-02-16
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra08163f
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A [3 + 3] and [3 + 2] annulation strategy using nitrostyrene derived MBH primary and secondary nitro allylic acetate for the construction of tetrahydrochromenes and dihydronaphthofurans at room temperature. Abstract : Substituted tetrahydrochromenes and dihydronaphthofurans are easily accessible by the treatment of β-tetralone with trans -β-nitro styrene derived Morita–Baylis–Hillman (MBH) acetates through a formal [3 + 3]/[3 + 2] annulation. The reaction proceeds through a cascade Michael/oxa-Michael pathway with moderate to good yields. A DFT study was carried out to account for the formation of the corresponding six and five-membered heterocycles via 6- endo-trig and 5- exo-trig cyclization.