A novel cyclization/oxidation strategy for a two-step synthesis of (Z)-aurone

• Published in: Tetrahedron letters Vol. 58; no. 14; pp. 1417 - 1420
• Main Authors: Li, Siyuan, Jin, Feng, Viji, Mayavan, Jo, Hyeju, Sim, Jaeuk, Kim, Hak Sung, Lee, Heesoon, Jung, Jae-Kyung
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 05.04.2017; Elsevier
• Subjects: (Z)-aurone; Cascade reaction; chemical structure; Chemistry; Chemistry, Organic; Fétizon oxidation; nitrates; organic compounds; oxidation; Oxygen heterocycles; Physical Sciences; potassium carbonate; Regio-selectivity; Science & Technology; silver; Silver (I) nitrate; Cascade reaction; (Z)-aurone; Silver (I) nitrate; Oxygen heterocycles; Regio-selectivity; Fétizon oxidation; Falzon oxidation; DESIGN; SERIES; SOLVENT; (z)-aurone; AGENTS; INHIBITORS; AURONE DERIVATIVES; FLAVONES
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.02.074

[Display omitted] •Two-step synthesis of (Z)-Aurones through cyclization/oxidation cascade reaction.•A novel AgNO3-promoted synthesis of diversely substituted aurones was developed.•(Z)-Aurones were obtained in good yields with excellent regio- and diastereoselectivity. An efficient and facile two-step strategy for the synthesis of (Z)-aurone from arylacetylenes and salicyladehydes, via silver(I) nitrate mediated cyclization/oxidation in the presence of potassium carbonate has been developed. The key feature of our method was delicate cascade reaction, to provide the corresponding (Z)-aurone in high yield and good regio- and stereo selectivity.