title: Base-promoted transannulation of heterocyclic enamines and 2,3-epoxypropan-1-ones: regio- and stereoselective synthesis of fused pyridines and pyrroles.
abstract: Base-promoted transannulation of heterocyclic enamines and 2,3-epoxypropan-1-ones has been successfully achieved, providing a new access to structurally diverse fused pyridines and pyrroles with excellent regio- and stereoselectivity. Treatment with N-aryl 4-aminofuran-2(5H)-ones and 2,3-epoxypropan-1-ones under microwave heating resulted in functional furo[3,2-b]pyridines in good yields. The N-aryl 4-aminopyrrol-2(5H)-ones bearing an electron-withdrawing group engaged in the reaction afforded pyrrolo[3,2-b]pyridines, whereas their counterparts with an electron-neutral or an electron-donating group underwent a different reaction pathway to form pyrrolo[3,2-b]pyrroles through C-C bond cleavage.
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Yang
authors.forename: Wen-Juan
authors.initials: WJ
authors.lastname: Hao
authors.forename: Hai-Wei
authors.initials: HW
authors.lastname: Xu
authors.forename: Shu-Liang
authors.initials: SL
authors.lastname: Wang
authors.forename: Bo
authors.initials: B
authors.lastname: Jiang
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D005663:Furans; D006571:Heterocyclic Compounds; D011725:Pyridines; D011758:Pyrroles