title: A synthesis of fused acenaphthopyrrolizines via the 1,3-dipolar cycloaddition reaction of azomethine ylides with acetylenic esters.
abstract: An efficient synthesis of tetraalkyl 6a-hydroxy-3-alkyl-3H,6aH-acenaphtho[1,2-g] pyrrolizine-1,2,5,6-tetracarboxylates via the 1,3-dipolar cycloaddition reaction of azomethine ylides (generated in situ from [Formula: see text]-amino acids and acenaphthylene-1,2-dione) with dialkyl acetylenedicarboxylates is described. When glycine was used instead of alanine, phenylalanine, valine, or isoleucine, dialkyl (E)-1[Formula: see text]-(1,4-dialkoxy-1,4-dioxobut-2-en-2-yl)-2-oxo-[Formula: see text],5[Formula: see text]-dihydro-2H-spiro [acenaphthylene-1,2[Formula: see text]-pyrrole]-3[Formula: see text],4[Formula: see text]-dicarboxylates were obtained. The steric effects of the [Formula: see text]-amino acids side chains may be responsible for their different behaviors.
authors.affiliation: Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran. yavarisa@modares.ac.ir.
authors.forename: Issa
authors.initials: I
authors.lastname: Yavari
authors.affiliation: Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.
authors.forename: Leila
authors.initials: L
authors.lastname: Baoosi
authors.affiliation: Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran.
authors.forename: Mohammad R
authors.initials: MR
authors.lastname: Halvagar
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004952:Esters / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001391:Azo Compounds; D004952:Esters; D011758:Pyrroles; D013882:Thiosemicarbazones; C512188:azomethine
keywords: 1, 3-Dipolar cycloaddition azomethine ylides; Acetylenic ester; Fused pyrrolizines; Spiro[acenaphthylenepyrrole]