Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

• Published in: Tetrahedron letters Vol. 138; p. 154962
• Main Authors: Li, Wei-Le, Liu, Bao-Yang, Li, Chun-Mei, Wang, Xiang, Hao, Wen-Juan, Jiang, Bo
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 24-03-2024
• Subjects: 1-Alkynylnaphthalen-2-ols; Alkyne-carbonyl metathesis; Cyclization; Oxa-Michael addition; Regioselectivity; Cyclization; Regioselectivity; Alkyne-carbonyl metathesis; Oxa-Michael addition; 1-Alkynylnaphthalen-2-ols
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2024.154962

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A new microwave-promoted Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization of 1-alkynylnaphthalen-2-ols with ninhydrin is reported, furnishing a wide range of naphtho[2,1-b]furan-1-ones with a quaternary center in good yields. Exchang ninhydrin for 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione resulted in functionalized pyrimidine-2,4,6-trione-containing naphtho[2,1-b]furan-1-ones. The catalytic cyclization protocol has attractive characteristics of high atom utilization, good compatibility with different types of substituents, and the efficient control of regiochemistry.