title: Metal-Free Reaction of ortho-Carbonylated Alkynyl-Substituted Arylaldehydes with Common Amines: Selective Access to Functionalized Isoindolinone and Indenamine Derivatives.
abstract: Herein we describe a reaction of ortho-carbonylated alkynyl-substituted arylaldehydes with common primary amines that can provide functionalized isoindolinone and 3-hydroxylindenamine products in high yields. Depending on the substituent size of primary amines, two distinct reaction pathways were exploited selectively, that are, an initial aza-conjugate addition followed by hydrogen transfer to access isoindolinone framework and a unique oxa-conjugate addition followed by Petasis-Ferrier rearrangement to afford indenamine derivatives. In the presence of Et3N, the reaction property of small primary amines was changed, proceeding to afford 3-hydroxylindenamine derivatives efficiently. These products contain interesting substructures that exist in many natural products and bioactive molecules. The reaction features contain the use of transition-metal-free catalysts, simple operation, broad substrate scope, and product diversity.
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Ziping
authors.identifier: http://orcid.org/0000-0001-6600-8599
authors.initials: Z
authors.lastname: Cao
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Hongbo
authors.initials: H
authors.lastname: Zhu
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Xin
authors.initials: X
authors.lastname: Meng
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Jun
authors.initials: J
authors.lastname: Guan
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Laijin
authors.initials: L
authors.lastname: Tian
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Xuejun
authors.initials: X
authors.lastname: Sun
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Guang
authors.initials: G
authors.lastname: Chen
authors.affiliation: School of Chemistry and Chemical Engineering, Qufu Normal University, Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu, 273165, Shandong, P. R. China.
authors.forename: Jinmao
authors.initials: J
authors.lastname: You
keywords: amines; heterocycles; indenamine; isoindolinone; ynones