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A. R. de Oliveira et al.
Paper
Synthesis
Diphenyl [Anilino(4-nitrophenyl)methyl]phosphonate21
Diphenyl [Anilino(4-methylphenyl)methyl]phosphonate21
Yellow solid; yield: 875 mg (95%); mp 149–151 °C.
IR (KBr): 3305.3 (N–H), 1182.1 (P=O), 772.0 (C–P) cm–1
Yellow solid; yield: 814 mg (95%); mp 120–123 °C.
IR (KBr): 3345.0 (N–H), 1215.1 (P=O), 764.6 (C–P) cm–1
.
.
1H NMR (300 MHz, CDCl3): δ = 8.19–8.22 (m, 2 H), 7.67–7.81 (m, 3 H),
6.75–7.34 (m, 12 H), 6.56–6.64 (m, 3 H), 5.30 (d, J = 25.4 Hz, 1 H, N–
CH–P).
1H NMR (300 MHz, CDCl3): δ = 8.17–7.91 (m, 1 H), 7.60–7.45 (m, 3 H),
7.40–7.10 (m, 12 H), 7.03–6.79 (m, 5 H), 6.68–6.58 (m, 2 H), 5.16 (d,
JH–P = 24.6 Hz, 1 H, N–CH–P).
13C NMR (75 MHz, CDCl3): δ = 149.9, 149.8, 147.7, 145.1, 144.9, 142.7,
125.7, 125.6, 123.8, 123.7, 123.6, 120.4, 120.3, 120.1, 120.0, 119.4,
118.9, 115.3, 113.8, 113.7, 76.5, (d, JC–P = 150.1 Hz) 56.7, 54.7.
13C NMR (75 MHz, CDCl3): δ = 150.2, 143.5, 143.2, 134.8, 129.7, 129.6,
129.4, 128.7, 128.2, 128.1, 125.3, 120.7, 120.6, 120.3, 120.2, 120.1,
115.6, 115.3, 114.1, 76.5, 56.2 (d, JC–P = 152.2 Hz), 20.4 (s, CH3).
MS: m/z = 461 [M + 1]+.
MS: m/z = 430 [M + 1]+.
Diphenyl [Anilino(4-chlorophenyl)methyl]phosphonate21
Diphenyl [Anilino(3-nitrophenyl)methyl]phosphonate21
Brown solid; yield: 814 mg (89%); mp 131–133 °C.
Yellow solid; yield: 800 mg (87%); mp 124–126 °C.
IR (KBr): 3299.0 (N–H), 1182.1 (P–O), 765.6 (C–P) cm–1
1H NMR (300 MHz, DMSO): δ = 7.51–7.57 (m, 3 H), 7.11–7.38 (m, 12
H), 6.64–6.98 (m, 5 H), 5.16 (d, J = 24.9 Hz, 1 H, N–CH–P).
13C NMR (75 MHz, CDCl3): δ = 150.1, 149.9, 145.5, 145.4, 134.2, 133.4,
129.7, 129.4, 129.3, 129.0, 128.9, 125.5, 125.3, 120.5, 120.5, 120.2,
119.1, 113.9, 76.5, 56.4 and 54.4 (d, JC–P = 153.0 Hz).
.
1H NMR (300 MHz, CDCl3): δ = 8.15–7.99 (m, 2 H), 7.61–7.11 (m, 12
H), 6.95–6.50 (m, 6 H), 5.30 (dd, J = 21.0, 1 H, N–CH–P).
13C NMR (75 MHz, CDCl3): δ = 151.5, 149.8, 138.9, 129.8, 129.6, 129.4,
129.0, 128.1, 128.1, 125.9, 125.8, 125.5, 120.4, 120.4, 120.2, 120.0,
115.7, 115.3, 113.2, 112.4, 55.7 and 54.4 (d, J C–P = 156.2 Hz).
MS: m/z = 461 [M + 1]+.
MS: m/z = 450 [M + 1]+.
Diphenyl {Anilino[4-(dimethylamino)phenyl]methyl}phospho-
nate21
Diphenyl [Anilino(4-fluorophenyl)methyl]phosphonate21
Orange solid; yield: 756 mg (90%); mp 98–100 °C.
IR (KBr): 3399.1 (N–H), 1188.9 (P=O), 772.3 (C–P) cm–1
Yellow solid; yield: 778 mg (90%); mp 125–127 °C.
IR (KBr): 3453.2 (N–H), 1284.6 (P–O), 776.8 (C-O) cm–1
.
.
1H NMR (300 MHz, CDCl3): δ = 7.79–7.75 (m, 1 H), 7.43–7.39 (m, 3 H),
7.32–7.10 (m, 11 H), 6.94–6.66 (m, 5 H), 5.10 (dd, J = 23.6, 1 H, N–CH–
P), 3.09 (s, 3 H), 2.94 (s, 3 H).
1H NMR (300 MHz, CDCl3) δ = 7.52–7.25 (m, 2 H), 7.03–7.33 (m, 12 H),
6.76–6.94 (m, 4 H), 6.63–6.66 (m, 2 H), 5.15 (d JH–P = 24.0 Hz, 1 H, N–
CH–P).4
13C NMR (75 MHz, CDCl3): δ = 150.1, 146.1, 145.8, 129.5, 129.4, 129.0,
128.8, 128.7, 125.0, 124.9, 121.5, 120.6, 120.5, 120.3, 119.6, 118.4,
115.3, 113.9, 112.5, 110.8, 112.5, 76.4, 56.3 and 54.2 (d, JP–C = 153.7
Hz), 40.3 (s, N–C).
13C NMR (75 MHz, CDCl3): δ = 150.1, 145.7, 145.5, 129.8, 129.8, 129.7,
129.3, 125.4, 125.3, 120.6, 120.5, 120.2, 120.1, 119.0, 115.9, 115.9,
115.6, 115.6, 113.9, 76.5, 56.2 and 54.2 (d, JC–P = 153.7 Hz).4
MS: m/z = 434 [M + 1]+.
MS: m/z = 459 [M + 1]+.
Diphenyl [Anilino(4-bromophenyl)methyl]phosphonate21
Diphenyl {Anilino[4-(trifluoromethyl)phenyl]methyl}phospho-
nate21
Brown solid; yield: 967 mg (98%); mp 140–142 °C.
IR (KBr): 3322.7 (N–H), 1029.6 (P–O), 765.6 (C–P) cm–1
.
Green solid; yield: 732 mg (91%); mp 118–120 °C.
1H NMR (300 MHz, CDCl3): δ = 7.50–7.42 (m, 4 H), 7.32–7.07 (m, 9 H),
6.95–6.91 (m, 2 H), 6.83–6.75 (m, 3 H), 6.63–6.61 (m, 2 H), 5.10 (d,
J = 24.9 Hz, 1 H, N–CH–P).
13C NMR (75 MHz, CDCl3): δ = 145.6, 145.4, 134.9, 134.0, 131.9, 129.7,
129.6, 129.3, 125.5, 125.4, 122.4, 120.5, 120.4, 120.2, 120.1, 119.1,
113.9, 100.0, 76.5, 56.4 and 54.4 (d, JC–P = 151.5 Hz).
IR (KBr): 3326.1 (N–H), 1209.6 (P=O), 752.1 (C–P) cm–1
.
1H NMR (300 MHz, CDCl3): δ = 7.73–7.44 (m, 5 H), 7.33–6.62 (m, 15
H), 5.22 (d, J = 25.4, 1 H, N–CH–P).
13C NMR (75 MHz, CDCl3): δ = 150.0, 145.4, 139.0, 129.8, 129.7, 129.5,
129.3, 128.5, 128.4, 125.6, 125.5, 120.5, 120.2, 120.1, 119.2, 115.3,
113.9, 56.3 and 55.0 (d, JP–C = 153.1 Hz).
MS: m/z = 495 [M + 1]+.
MS: m/z = 484 [M + 1]+.
Diphenyl [Anilino(4-methoxyphenyl)methyl]phosphonate21
Diphenyl [Anilino(3-hydroxyphenyl)methyl]phosphonate21
Yellow solid; yield: 871 mg (98%); mp 141–143 °C.
Semi-solid; yield: 774 mg (90%).
IR (KBr): 3329.0 (N–H), 1252.0 (P–O), 770.4 (C–P) cm–1
.
IR (KBr): 3298.1 (N–H), 1280.0 (P=O), 770.4 (C–P) cm–1
.
1H NMR (300 MHz, CDCl3): δ = 7.51–7.45 (m, 2 H), 7.33–7.09 (m, 13
H), 6.93–6.65 (m, 5 H), 5.12 (d, J = 25.38 Hz, 1 H, N–CH–P), 3.80 (s, 3
H).
13C NMR (75 MHz, CDCl3): δ = 150.3, 150.0, 145.9, 145.7, 129.6, 129.5,
129.3, 129.2, 129.1, 126.4, 126.3, 125.2, 125.1, 120.6, 120.5, 120.3,
120.2, 118.6, 114.2, 114.1, 113.9, 76.5, 56.2, 56.2 and 55.1, 54.1 (t, JC–P
155.2 Hz).
1H NMR (300 MHz, CDCl3): δ = 7.36–7.04 (m, 6 H), 6.90–6.73 (m, 8 H),
6.47–6.34 (m, 2 H), 6.05 (s, 1 H, O-H), 4.96–4.84 (m, 3 H), 3.74 and
3.73 (dd, JH–P = 15.0 Hz, JH–C = 21.0, 1 H, N–CH–P), 1.25 (s, 1 H).
13C NMR (75 MHz, CDCl3): δ = 156.40, 156.39, 146.02, 145.90, 135.99,
134.51, 134.31, 129.92, 129.82, 129.50, 128.61, 128.17, 126.76,
125.54, 123.81, 122.06, 120.78, 120.73, 120.69, 120.42, 119.95,
119.08, 115.50, 115.50, 114.04, 54.97 and 53.02 (d, JP–C = 151.10 Hz).
=
MS: m/z = 446 [M + 1]+.
MS: m/z = 432 [M + 1]+.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–F