title: Synthesis of novel and diverse naphtho[1,2-b]furans by phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and acetylenecarboxylates.
abstract: A new phosphine-catalyzed [3+2] annulation reaction between activated 1,4-naphthoquinones and acetylenecarboxylates is described. This reaction provides a facile and efficient route to a variety of biologically promising and novel naphtho[1,2-b]furans. This devised method provides a first example for the synthesis of diverse naphtho[1,2-b]furan derivatives from 1,4-naphthoquinones via phosphine-catalyzed [3+2] annulation. A variety of novel naphtho[1,2-b]furans were synthesized via the phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and electron-deficient acetylenecarboxylates. In some reactions, both furannulation adducts and reductive/nucleophilic conjugate addition products were produced.
authors.affiliation: School of Chemical Engineering, Yeungnam University, Gyeongsan, 712-749, Republic of Korea.
authors.forename: Likai
authors.initials: L
authors.lastname: Xia
authors.forename: Krishna Bahadur Somai
authors.initials: KB
authors.lastname: Magar
authors.forename: Yong Rok
authors.initials: YR
authors.lastname: Lee
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D009285:Naphthoquinones / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D005663:Furans; D009285:Naphthoquinones; D010720:Phosphines; C044646:phosphine; D000114:Acetylene; C035342:1,4-naphthoquinone