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Organic & Biomolecular Chemistry
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ARTICLE
transferred to a glass chromatography column (silica gel; diameter = 4'-fluoro-1'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione
DOI: 10.1039/D0OB01104E
4 cm, lengh = 20 cm).
regioisomers; Rf = 0.79 (7:3 EtOAc/Hexane); 1H NMR (300 MHz,
1'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione8b(6a): White CDCl3) δ 7.31–7.22 (m, 1H), 6.86–6.76 (m, 1H), 6.68–6.62 (m, 1H),
solid, 91% yield; Rf = 0.8 (EtOAc); 1H NMR (300 MHz, CDCl3) δ 7.43– 4.57 (d, J = 9.0 Hz, 1H), 4.33 (d, J = 9.0 Hz, 1H), 3.24 (s, 3H), 3.15 (d, J
7.30 (m, 2H), 7.18–7.10 (m, 1H), 6.91 (d, J = 9.0 Hz, 1H), 4.59 (d, J = = 18.0 Hz, 1H), 2.65 (d, J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ
9.0 Hz, 1H), 4.36 (d, J = 9.0 Hz, 1H), 3.26 (s, 3H), 3.16 (d, J = 18.0 Hz, 175.71, 174.04, 163.70 (d, JC,F = 246.0 Hz), 144.41 (d, JC,F = 11.25 Hz),
1H), 2.67 (d, J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 175.38, 126.16 (d, JC,F = 2.25 Hz), 123.47 (d, JC,F = 9.75 Hz), 109.75 (d, JC,F
174.38, 142.73, 130.86, 129.51, 123.69, 122.27, 108.80, 74.81, 50.68, 22.5 Hz), 97.83 (d, JC,F = 27.0 Hz), 74.74, 50.37, 38.46, 26.83. MS-EI:
=
38.43, 26.69. MS-EI: m/z (%) 217 (M+, 35), 159 (100).
1',5'-dimethyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione
m/z(%) 235 (M+, 27), 177(100). HRMS (ESI-TOF) calcd for C12H10FNO3
(6b): [M+H]+ 236.0722, found 236.0716.
White solid, 92% yield; Rf = 0.8 (EtOAc); 1H NMR (300 MHz, CDCl3) δ 6'-fluoro-1'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione
7.19–7.12 (m, 2H), 6.79 (d, J = 9.0 Hz, 1H), 4.58 (d, J = 9.0 Hz, 1H), (6h): Off-white solid, 48% of a total 80% yield, considering both
4.34 (d, J = 9.0 Hz, 1H), 3.23 (s, 3H), 3.16 (d, J = 18.0 Hz, 1H), 2.65 (d, regioisomers; Rf = 0.62 (7:3 EtOAc/Hexane); 1H NMR (300 MHz,
J = 18.0 Hz, 1H), 2.35 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 175.20, CDCl3) δ 7.40–7.30 (m, 1H), 6.89–6.80 (m, 1H), 6.72 (d, J = 9.0 Hz, 1H),
174.50, 140.26, 133.49, 130.99, 129.65, 123.04, 108.51, 74.91, 50.77, 4.56 (d, J = 9.0 Hz, 1H), 4.47 (d, J = 9.0 Hz, 1H), 3.25 (s, 3H), 3.09 (d, J
38.47, 26.69, 21.01. MS-EI: m/z (%) 231 (M+, 29), 173 (100). HRMS = 18.0 Hz, 1H), 2.85 (d, J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ
(ESI-TOF) calcd for C13H13NO3 [M+H]+ 232.0973, found 232.0968.
175.54, 173.95, 158.65 (d, JC,F = 246.0 Hz), 144.99 (d, JC,F = 9.0 Hz),
131.33 (d, JC,F = 8.25 Hz), 115.85 (d, JC,F = 20.25 Hz), 110.98 (d, JC,F
5'-fluoro-1'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione8b
=
1
(6c): White solid, 64% yield; Rf = 0.82 (EtOAc); H NMR (300 MHz, 20.25 Hz), 104.97 (d, JC,F = 3.0 Hz), 73.27, 49.74, 36.91, 27.14. MS-EI:
CDCl3) δ 7.15–7.03 (m, 2H), 6.89–6.81 (m, 1H), 4.58 (d, J = 9.0 Hz, 1H), m/z(%) 235 (M+, 25), 177(100). HRMS (ESI-TOF) calcd for C12H10FNO3
4.35 (d, J = 9.0 Hz, 1H), 3.25 (s, 3H), 3.17 (d, J = 18.0 Hz, 1H), 2.67 (d, [M+H]+ 236.0722, found 236.0720.
J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 174.99, 173.84, 159.64 5'-methoxy-1'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-
(d, JC,F = 241.5 Hz), 138.71, 132.18 (d, JC,F = 8.25 Hz), 115.84 (d, JC,F
23.25 Hz), 110.68 (d, JC,F = 25.5 Hz), 109.48 (d, JC,F = 7.5 Hz), 74.46, 1H NMR (300 MHz, CDCl3) δ 6.94–6.77 (m, 3H), 4.58 (d, J = 9.0 Hz, 1H),
=
dione8b (6i): Off-white solid, 68% yield; Rf = 0.48 (3:7 EtOAc/Hexane);
51.08, 38.30, 26.84. MS-EI: m/z(%) 235 (M+, 27), 177(100).
7'-fluoro-1'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione
4.35 (d, J = 9.0 Hz, 1H), 3.80 (s, 3H), 3.23 (s, 3H), 3.17 (d, J = 18.0 Hz,
1H), 2.66 (d, J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 174.99,
(6d): Off-white solid, 80% yield; Rf = 0.78 (7:3 EtOAc/Hexane); 1H 174.34, 156.80, 136.02, 132.07, 113.85, 109.50, 109.27, 74.81, 55.92,
NMR (300 MHz, CDCl3) δ 7.15–7.04 (m, 3H), 4.58 (d, J = 9.0 Hz, 1H), 51.09, 38.44, 26.75. MS-EI: m/z(%) 247 (M+, 53), 174(100).
4.35 (d, J = 9.0 Hz, 1H), 3.47 (d, JH,F = 3.0 Hz, 3H), 3.17 (d, J = 18.0 Hz, 1'-methyl-7'-phenyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione
1H), 2.67 (d, J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 174.95, (6j): Off-white solid, 77% yield; Rf = 0.81 (3:7 EtOAc/Hexane); 1H NMR
173.97, 147.83 (d, JC,F = 243.75 Hz), 133.66, 129.45 (d, J = 8.25 Hz), (300 MHz, CDCl3) δ 7.43 (m, 3H), 7.39–7.29 (m, 3H), 7.21–7.10 (m,
124.47 (d, JC,F = 6.75 Hz), 118.08 (d, J = 3.0 Hz), 117.51 (d, J = 18.75 2H), 4.62 (d, J = 9.0 Hz, 1H), 4.41 (d, J = 9.0 Hz, 1H), 3.20 (d, J = 18.0
Hz), 74.74, 50.94, 38.63, 29.20 (d, JC,F = 5.25 Hz). MS-EI: m/z(%) 235 Hz, 1H), 2.76 (s, 3H), 2.73 (d, J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3)
(M+, 34), 177(100). HRMS (ESI-TOF) calcd for C12H10FNO3 [M+H]+ δ 176.41, 174.43, 139.57, 138.09, 132.43, 131.86, 129.76, 128.04,
236.0722, found 236.0715.
127.96, 126.27, 122.99, 121.25, 75.14, 50.07, 38.87, 30.60. MS-EI:
m/z(%) 293 (M+, 54), 235(100). HRMS (ESI-TOF) calcd for C18H15NO3
5'-chloro-1'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione8b
(6e): White solid, 70% yield; Rf = 0.60 (7:3 EtOAc/Hexane); H NMR [M+H]+ 294.1130, found 294.1121.
1
(300 MHz, CDCl3) δ 7.39–7.29 (m, 2H), 6.84 (d, J = 9.0 Hz, 1H), 4.57 1'-benzyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione (6k): White
1
(d, J = 9.0 Hz, 1H), 4.35 (d, J = 9.0 Hz, 1H), 3.25 (s, 3H), 3.16 (d, J = 18.0 solid, 74% yield; Rf = 0.88 (3:7 EtOAc/Hexane); H NMR (300 MHz,
Hz, 1H), 2.67 (d, J = 18.0 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 174.85, CDCl3) δ 7.37–7.22 (m, 7H), 7.13–7.05 (m, 1H), 6.81 (d, J = 9.0 Hz, 1H),
173.77, 141.28, 132.32, 129.47, 129.09, 122.92, 109.77, 74.41, 50.83, 4.93 (s, 2H), 4.65 (d, J = 9.0 Hz, 1H), 4.40 (d, J = 9.0 Hz, 1H), 3.22 (d, J
38.28, 26.82. MS-EI: m/z(%) 251 (M+, 32), 196 (100).
= 18 Hz, 1H), 2.73 (d, J = 18 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ
175.62, 174.25, 141.88, 135.08, 130.72, 129.41, 128.95, 127.98,
127.30, 123.70, 122.37, 109.79, 74.83, 50.69, 44.26, 38.52. MS-EI:
1'-methyl-5'-(trifluoromethyl)-2H-spiro[furan-3,3'-indoline]-
2',5(4H)-dione (6f): White solid, 75% yield; Rf
= 0.71 (7:3 m/z(%) 293 (M+, 22), 91(100). HRMS (ESI-TOF) calcd for C18H15NO3
EtOAc/Hexane); 1H NMR (300 MHz, CDCl3) δ 7.67 (d, J = 9.0 Hz, 1H), [M+H]+ 294.1130, found 294.1120.
7.55 (s, 1H), 7.00 (d, J = 9.0 Hz, 1H), 4.59 (d, J = 9.0 Hz, 1H), 4.38 (d, J 1'-benzyl-5'-methyl-2H-spiro[furan-3,3'-indoline]-2',5(4H)-dione
1
= 9.0 Hz, 1H), 3.30 (s, 3H), 3.19 (d, J = 18.0 Hz, 1H), 2.71 (d, J = 18.0 (6l): White solid, 80% yield; Rf = 0.88 (3:7 EtOAc/Hexane); H NMR
Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 175.35, 173.56, 149.10, 145.74, (300 MHz, CDCl3) δ 7.38–7.23 (m, 5H), 7.14 (s, 1H), 7.04 (d, J = 9.0 Hz,
131.29, 127.33 (q, JC,F = 3.75 Hz), 123.96 (q, JC,F = 285.0 Hz), 119.58 (q, 1H), 6.69 (d, J = 9.0 Hz, 1H), 4.91 (s, 2H), 4.64 (d, J = 9.0 Hz, 1H), 4.39
JC,F = 3.75 Hz), 108.68, 74.29, 50.58, 38.24, 26.92. MS-EI: m/z(%) 285 (d, J = 9.0 Hz, 1H), 3.21 (d, J = 18.0 Hz, 1H), 2.70 (d, J = 18.0 Hz, 1H),
(M+, 26), 227(100). HRMS (ESI-TOF) calcd for C13H10F3NO3 [M+H]+ 2.31 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 175.47, 174.40, 139.40,
286.0691, found 286.0686.
135.21, 133.53, 130.86, 129.61, 128.92, 127.91, 127.28, 123.13,
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