title: Fused Multifunctionalized Chromenes from Tetraynes and α,β-Unsaturated Aldehydes.
abstract: The synthesis of fused, highly substituted chromenes in a one-pot-three-step cascade hexadehydro-Diels-Alder reaction of tetraynes followed by an intermolecular α,β-unsaturated aldehyde rearrangement is reported. The target compounds were prepared by the condensation of malonates with 3-bromo-1-propyne, and the resulting 2,2-di(1-propyn-3-yl)malonates underwent cross-coupling with phenylethynyl bromides to afford 2,2-di(5-phenyl-2,4-pentadiynyl)malonates, which underwent intramolecular cyclization to produce tricyclic chromenes. The overall transformation involves the formation of four new C-C bonds and one new C-aryl-O-C-aryl bond by both intramolecular cyclization and intermolecular rearrangement reactions. These constitute a key strategy for the construction of a highly substituted natural chromene core and a robust method for producing other chromenes.
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, P. R. China.
authors.forename: Xiangzhen
authors.initials: X
authors.lastname: Meng
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, P. R. China.
authors.forename: Shuang
authors.initials: S
authors.lastname: Lv
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, P. R. China.
authors.forename: Dong
authors.initials: D
authors.lastname: Cheng
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, P. R. China.
authors.forename: Qiong
authors.initials: Q
authors.lastname: Hu
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, P. R. China.
authors.forename: Jie
authors.initials: J
authors.lastname: Ma
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, P. R. China.
authors.forename: Baohua
authors.initials: B
authors.lastname: Liu
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, P. R. China.
authors.forename: Yimin
authors.identifier: http://orcid.org/0000-0002-1638-5393
authors.initials: Y
authors.lastname: Hu
keywords: condensed chromene compounds; cross-coupling; cyclization; hexadehydro-Diels-Alder reaction; unsaturated aldehydes