Synthesis of naphthoxindoles, anthraoxindoles and phenanthrofuranones from arynes

• Published in: Tetrahedron Vol. 75; no. 45; pp. 130638 - 130646
• Main Authors: Xiao, Peng, Cao, Weiguo, Chen, Jie, Chen, Yali
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.11.2019; Elsevier
• Subjects: Anthraoxindoles; aromatization; Arynes; chemical structure; Chemistry; Chemistry, Organic; cycloaddition reactions; dehydrogenation; fluorescence; Methylenebenzofuranones; Methyleneindolinones; Naphthoxindoles; organic compounds; Phenanthrofuranones; Physical Sciences; Science & Technology; thermal properties; Naphthoxindoles; Methyleneindolinones; Methylenebenzofuranones; Anthraoxindoles; Phenanthrofuranones; Arynes; ARISTOLACTAMS; DIOXOAPORPHINES; CONSTRUCTION; NAPHTHO-FUSED OXINDOLES; ALKALOIDS
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2019.130638

An efficient process for the synthesis of naphthoxindoles, anthraoxindoles and phenanthrofuranones by Diels−Alder reactions and dehydrogenation aromatization reactions of benzyne or naphthyne with methyleneindolinones or methylenebenzofuranones in good yields. The photophysical, redox, and thermal properties of oxadisilole fused naphthoxindoles and anthraoxindoles have been determined. This compounds show potential applications for organic light-emitting materials due to their high fluorescence quantum yields and thermal stabilities. [Display omitted] •An efficient and convenient method was studied for the synthesis of products.•This reaction provides wide universality.•The products show potential applications for organic light-emitting materials.