title: Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles.
abstract: A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides. The reaction pathway involves Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm rearrangement and an oxo-Diels-Alder reaction sequence, resulting in continuous multiple bond-forming events including C-N, C-O and C-H bonds to rapidly build up molecular complexity.
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. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
authors.forename: Qian
authors.initials: Q
authors.lastname: Gao
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. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
authors.forename: Wen-Juan
authors.initials: WJ
authors.lastname: Hao
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. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
authors.forename: Feng
authors.initials: F
authors.lastname: Liu
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. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
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. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
authors.forename: Shu-Liang
authors.initials: SL
authors.lastname: Wang
authors.affiliation: Institute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University, Nanjing 210093, P. R. China and Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA. guigen.li@ttu.edu.cn.
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
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. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
authors.forename: Bo
authors.initials: B
authors.lastname: Jiang
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D003998:Dicarboxylic Acids / Q000737:chemistry*; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; D003486:Cyanides; D003998:Dicarboxylic Acids; D007094:Imides; D011714:Pyrans; C036658:acrylic acid