M. R. Mahran, M. D. Khidre, W. Abdou
Apr 1, 1995
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0
Influential Citations
15
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Journal
Phosphorus Sulfur and Silicon and The Related Elements
Abstract
Abstract 5-Methylisatin ( 1b) reacts with TAP ( 4a–c) and/or DAP ( 3a-c) to give the respective dialkyl α-hydroxyphosphonates (8a-c). Isatin-monoxime ( 5a) and 5-methyl isatin-monoxime ( 5b) react with alkyl phosphites to give dialkyl 2-oxo-indolyl phosphorates ( 8a–c, 12a–f, 15a–c) as major products. The carbonyl-group at position – 3 in 1b is deoxygenated by triphenylphosphine to give a new phosphorus ylide ( 17 ) and by methylenetriphenylphosphoranes (Wittig-reagents, 7a-c) to afford the respective 3- substituted methylenes ( 19a-c) in good yields. Possible reaction mechanisms were considered and structural assignments were based upon analytical, chemical and spectroscopic (IR, 1H NMR, 31P NMR and MS) results.