Reaction between naphthols and dimethyl acetylenedicarboxylate in the presence of phosphites. Synthesis of stable oxa-2 lambda 5-phosphaphenanthrenes,and benzochromene derivatives |
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Authors: | Yavari Issa Anary-Abbasinejad Mohammad Hossaini Zinatossadat |
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Institution: | Department of Chemistry, University of Tarbiat Modarres, PO Box 14115-175, Tehran, Iran. isayavar@yahoo.com |
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Abstract: | The reaction of dimethyl acetylenedicarboxylate (DMAD) with 2-naphthol in the presence of trimethyl or triphenyl phosphite leads to stable dimethyl oxa-2 lambda 5-phosphaphenanthrene derivatives in good yields. The reaction of DMAD and trimethyl phosphite in the presence of 1-naphthol or 8-hydroxyquinoline leads to dimethyl 2-(dimethoxyphosphoryl)-3-(1-hydroxy-2-naphthyl)succinate or dimethyl 2-(dimethoxyphosphoryl)-3-(8-hydroxyquinolin-7-yl)-succinate in excellent yields. Using triethyl phosphite and DMAD in the presence of 2-naphthol or 1-naphthol produces methyl 3-oxo-2,3-dihydro-1H-benzof]chromene-1-carboxylate or methyl 2-oxo-3,4-dihydro-2H-benzoh]-chromene-4-carboxylate in excellent yields. |
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