title: A [3 + 2]-annulation approach to tetrasubstituted furans from MBH-carbonates of acetylenic aldehydes via sequential substitution/cycloisomerization.
abstract: A novel metal-free approach to construct the tetrasubstituted furans from Morita-Baylis-Hillman (MBH)-carbonates of acetylenic aldehydes has been developed. This strategy involves the cascade nucleophilic substitution/5-exo-dig-cycloisomerization of MBH-carbonates with 1,3-dicarbonyl compounds to give uniquely substituted 2-furan-3-yl acrylates. Additionally, the obtained furan adducts open a new entry to naphthofurans through palladium-catalyzed decarboxylative benzannulation.
authors.affiliation: Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. rajireddy@iict.res.in.
authors.forename: Chada Raji
authors.initials: CR
authors.lastname: Reddy
authors.forename: Siddique Z
authors.initials: SZ
authors.lastname: Mohammed
authors.forename: Paridala
authors.initials: P
authors.lastname: Kumaraswamy
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism
chemical_list: D000447:Aldehydes; D002254:Carbonates; D005663:Furans; D000114:Acetylene; C039281:furan