Phosphorated 1,2-Oxazabuta-1,3-dienes as Synthetic Tools for the Preparation of α-Amino Phosphorus Derivatives and Functionalized Nitrogen-Containing Heterocycles

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• “ Representative procedure for the synthesis of α-amino-phosphine oxide 9a: To an ice-cooled solution of α-bromooxime 3a (352 mg, 1.0 mmol) in dichlorometane (5 mL), triethylamine (140 μL, 1.0 mmol) was added. Then p-anisidine (123 mg, 1.0 mmol) was added all at once. The reaction was allowed to stir at room temperature for 30 min. The solvent was removed by rotary evaporation, and the residue was stirred with diethyl ether; then it was filtered through a sintered glass vacuum filtration funnel. The solid was washed twice with ether, and the filtrate was concentrated to dryness in vacuum. The crude products were purified by flash-column chromatography (silica gel, AcOEt) to afford α-amino-phosphine oxide 9a (354 mg, 90%) obtained as a colorless oil. IR (NaCl) λ max 3341, 2929, 2673, 1514, 1434, 1242, 1167, 1028 cm-1; 1H NMR (400 MHz, CDCl3) δ 9.84 (1H, br s), 7.80–7.31 (10H, m), 6.60 (4H, s), 4.94–4.89 (1H, m), 4.82 (1H, dd, 3 J PH = 9.9 Hz, 3 J HH = 7.0 Hz), 3.62 (3H, s), 1.78 (3H, d, 4 J PH = 2.1 Hz); 13C NMR (75 MHz, CDCl3) δ 154.2, 152.8, 140.1, 140.0, 132.2, 132.2, 132.1, 132.0, 131.7, 131.6, 131.2, 131.1, 130.4, 129.8, 128.6, 128.5, 128.4, 128.2, 115.4, 114.7, 58.3 (d, 1 J PC = 76.1 Hz), 55.5, 11.4; 31P NMR (120 MHz, CDCl3) δ 32.1; MS (CI) m/z 395 (M++1, 100). Anal. Calcd for C22H23N2O3P: C, 67.00; H, 5.88; N, 7.10. Found: C, 67.01; H, 5.90; N, 7.09 ” .
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• “ Representative procedure for the synthesis of N-hydroxypyrrole 14a: To a stirred solution of α-bromooxime 3a (352 mg, 1.0 mmol) in CH2Cl2 (5 mL), triethylamine (1.2 mmol) was added. Then (E)-1-(3-methylbut-1-enyl)pyrrolidine 12a (167 mg, 1.2 mmol) was added all at once at room temperature under a nitrogen atmosphere. The reaction was allowed to stir at room temperature for 20 min. The solvent was removed by rotary evaporation, and the residue was stirred with diethyl ether. The triethyl amine hydrobromic salt was filtered through a sintered glass vacuum filtration funnel. The solid was washed twice with ether, and the filtrate was concentrated to dryness in vacuum to get N-hydroxypyrrole 14a (245 mg, 89%) obtained as a brown oil. IR (NaCl) obtained as a brown oil. IR (NaCl) λ max 3423, 2961, 1214, 1031, 963 cm-1; 1H NMR (300 MHz, CDCl3) δ 11.16 (bs, 1H), 6.53 (d, 4 J PH = 6.0 Hz, 1H), 4.02-3.92 (m, 4H), 3.00 (m, 1H), 1.98 (s, 3H), 1.29 (t, 3 J HH = 7.2 Hz, 6H), 1.13 (d, 3 J PH = 6.9 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 133.6 (d, 2 J PC = 26.0 Hz), 129.8 (d, 2 J PC = 12.5 Hz), 114.1 (d, 3 J PC = 13.5 Hz), 94.7 (d, 1 J PC = 218.4 Hz), 61.3 (d, 2 J PC = 5.6 Hz), 25.5, 24.5, 16.1 (d, 3 J PC = 7.0 Hz), 9.2; 31P NMR (120 MHz, CDCl3) δ 21.9; MS (EI) m/z 275 (M+, 10), 258 (100), 202 (40); HRMS (EI) m/z Calcd. for C12H22NO4P [M+] 275.1286, found: [M+] 275.1263 ” .
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