Synthesis of furanophane derivatives through [8+2]-cycloaddition of dienylisobenzofurans and alkynes.
The coupling of various dienylisobenzofurans with dimethyl acetylenedicarboxylate (DMAD) has been examined. In most cases, this reaction proceeds via [8+2]-cycloaddition to afford furan-bridged decatetraene ring systems. The major competing reaction pathway is [4+2]-cycloaddition between DMAD and the isobenzofuran nucleus. Isobenzofuran intermediates were generated using either a chromium carbene-based method or an acid-catalyzed method.
Luo
Yumei
Y
Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.
Herndon
James W
JW
Cervantes-Lee
Francisco
F
D000480:Alkynes / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001577:Benzophenones / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure
D000480:Alkynes; D001572:Benzofurans; D001577:Benzophenones