BF3·OEt2-catalyzed synthesis of 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran and trans-fused hexahydropyrano[3,2-c]chromene derivatives |
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| Authors: | Ch. Syama Sundar M. Ramana Reddy B. Sridhar S. Kiran Kumar C. Suresh Reddy B.V. Subba Reddy |
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| Affiliation: | 1. Department of Chemistry, Sri Venkateswara University, Tirupathi 517502, AP, India;2. Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;3. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;4. Centre for Nuclear Magnetic Resonance, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India |
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| Abstract: | A novel intramolecular Prins cyclization of (E)-5-(2-(hydroxymethyl)phenyl)pent-4-en-1-ol with aldehydes has been achieved using 10 mol % BF3·Et2O to produce 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran derivatives in good to excellent yields with high selectivity. Similar type of coupling with salicylaldehydes provides the trans-fused hexahydropyrano[3,2-c]chromene derivatives in excellent yields. |
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