FULL PAPER
8.6 Hz, 2H, ArH); 13C NMR (CDCl3): δ 22.5 (Cy), 25.0 (Cy),
Spiro[cyclohexane-1,3’-6’-(4-methylphenyl)-4’-
34.0–34.5 (m, Cy), 69.1 (CH2), 88.4 (OÀ C), 115.5 (Ar), 121.8
(q, J=274.7 Hz, CF3), 128.6 (Ar), 132.1 (Ar), 136.4 (Ar),
139.5 (Ar), 141.4 (q, J=35.1 Hz, CF3À C), 154.49 (Ar), 154.54
(Ar); 19F NMR (CDCl3, CFCl3): δ À 62.24 (s, 3F); IR (KBr)
2973, 2931, 2846, 1607, 1190, 1374, 1146, 832 cmÀ 1; HRMS
(FAB): calcd for [M+H]+ C20H18BrF3NO: 312.0524, Found:
312.0535.
trifluoromethyl-[1H]-furo[3,4-c]pyridine] (3°bA)
Yield: 80% (134 mg); White solid, M.p. 138.2-138.6 C, Eluent
of the column chromatography: Hexane/EtOAc=20/1; 1H
NMR (CDCl3): δ 1.25–1.44 (m, 1H, CyH), 1.53–1.84 (m, 7H,
CyH), 2.04 (td, J=13.0, 5.1 Hz, 2H, CyH), 2.41 (s, 3H, CH3),
5.06 (s, 2H, CH2), 7.29 (d, J=8.1 Hz, 2H, ArH), 7.73 (s, 1H,
ArH), 7.94 (d, J=8.1 Hz, 2H, ArH); 13C NMR (CDCl3): δ 21.3
(CH3), 22.5 (Cy), 25.0 (Cy), 34.0–34.2 (m, Cy), 34.0–35.0 (m,
Cy), 69.1 (OÀ CH2), 88.3 (OÀ C), 115.4 (Ar), 122.0 (q, J=
274.6 Hz, CF3), 126.9 (Ar), 129.6 (Ar), 134.8 (Ar), 138.7 (Ar),
139 9 (Ar), 141.2 (q, J=35.1 Hz, CF3À C), 154.1 (Ar), 155.8
(Ar); 19F NMR (CDCl3, CFCl3): δ À 62.20 (s, 3F); IR (KBr)
2943, 2655, 1605, 1448, 1373, 1126, 1046, 906 cmÀ 1; HRMS
(FAB): calcd for [M+H]+ C20H21F3NO: 348.1575, Found:
348.1585.
Spiro[cyclohexane-1,3’-4’-trifluoromethyl-6’-
(3,5-bistrifluoromethylphenyl)-[1H]-furo[3,4-c]
pyridine] (3fA)
°
Yield: 71% (178 mg); White solid, M.p. 123.3–124.0 C, Eluent
of the column chromatography: Hexane/EtOAc=20/1; 1H
NMR (CDCl3): δ 1.21–1.44 (m, 1H, CyH), 1.65–1.90 (m, 7H,
CyH), 2.05 (td, J=12.9, 4.9 Hz, 2H, CyH), 5.12 (s, 2H, CH2),
7.86 (s, 1H, ArH), 7.95 (s, 1H, ArH), 8.50 (s, 1H, ArH); 13C
NMR (CDCl3): δ 22.5 (Cy), 25.0 (Cy), 34.1–34.3 (m, Cy), 69.1
(OÀ CH2), 88.6 (OÀ C), 116.3 (Ar), 121.8 (q, J=274.6 Hz, CF3),
123.39 (q, J=272.7 Hz, CF3), 123.0–123.5 (m, Ar), 127.2–
127.3 (m, Ar), 132.5 (q, J=33.5 Hz, CF3À C), 139.7 (Ar), 141.0
(Ar), 142.1 (q, J=35.8 Hz, CF3À C), 152.6 (Ar), 155.4 (Ar); 19F
NMR (CDCl3, CFCl3): δ À 63.37 (s, 6F), À 62.27 (s, 3F); IR
(KBr) 2936, 2852, 1606, 1447, 1344, 1273, 1108, cmÀ 1; HRMS
(FAB): calcd for [M+H]+ C21H17F9NO: 470.1166, Found:
470.1172.
Spiro[cyclohexane-1,3’-6’-(4-aminophenyl)-4’-
trifluoromethyl-[1H]-furo[3,4-c]pyridine] (3cA)
°
Yield: 83% (143 mg); Yellow solid, M.p. 158.2–159.2 C,
Eluent of the column chromatography: Hexane/EtOAc=3/2; 1H
NMR (CDCl3): δ 1.25–1.39 (m, 1H, CyH), 1.55–1.81 (m, 7H,
CyH), 2.02 (td, J=13.0, 5.1 Hz, 2H, CyH), 3.87 (bs, 2H, NH2),
5.02 (d, J=0.68 Hz, 2H, CH2), 6.74 (d, J=8.6 Hz, 2H, ArH),
7.62 (s, 1H, ArH), 7.88 (d, J=8.6 Hz, 2H, ArH); 13C NMR
(CDCl3): δ 22.6 (Cy), 25.0 (Cy), 34.0–34.5 (m, Cy), 69.1
(OÀ CH2), 88.3 (OÀ C), 114.3 (Ar), 115.1 (Ar), 121.1 (q, J=
274.5 Hz, CF3), 127.8 (Ar), 128.4 (Ar), 137.7 (Ar), 141.0 (q,
J=34.9 Hz, CF3À C), 148.2 (Ar), 153.9 (Ar), 155.8 (Ar); 19F
NMR (CDCl3, CFCl3): δ À 62.22 (s, 3F); IR (KBr) 3478, 3384,
2926, 2361, 1636, 1370, 1186, 1116 cmÀ 1; HRMS (FAB): calcd
for [M+] C19H19F3N2O: 348.1449, Found: 348.1454.
Spiro[cyclohexane-1,3’-6’-
(2,3,4,5,6-pentafluorophenyl)-4’-trifluoromethyl-
[1H]-furo[3,4-c]pyridine] (3gA)
Yield: 71% (149 mg); Colorless oil, Eluent of the column
1
chromatography: Hexane/EtOAc=20/1; H NMR (CDCl3): δ
1.25–1.45 (m, 1H, CyH), 1.69–1.90 (m, 7H, CyH), 2.05 (td, J=
12.7, 5.2 Hz, 2H, CyH), 5.10 (s, 2H, CH2), 7.52 (s, 1H, ArH);
13C NMR (CDCl3): δ 22.5 (Cy), 25.0 (Cy), 34.0 (q, J=2.6 Hz,
Cy), 69.1 (OÀ CH2), 88.8 (OÀ C), 114.2 (td, J=15.9, 3.4 Hz,
CÀ F), 121.6 (q, J=274.8 Hz, CF3), 121.9 (Ar), 138.0 (dm, J=
253.5 Hz, FÀ C), 141.8 (dm, J=256.3 Hz, FÀ C), 142.3 (q, J=
36.0 Hz, CF3À C), 145.0 (dm, J=251.6 Hz, FÀ C), 145.3 (Ar),
154.7 (Ar); 19F NMR (CDCl3, CFCl3): δ À 161.68 (td, J=21.5,
7.6 Hz, 2F), À 152.94 (t, J=21.5 Hz, 1F), À 143.21 (dd, J=
21.5, 7.6 Hz, 2F); IR (neat) 2935, 2857, 1655, 1606, 1524,
1499, 1373, 1292, 1200, 1138, 993 cmÀ 1; HRMS (FAB): calcd
for [M+H]+ C19H14F8NO: 424.0948, Found: 424.0956.
Spiro[cyclohexane-1,3’-6’-(4-hydroxyphenyl)-4’-
trifluoromethyl-[1H]-furo[3,4-c]pyridine] (3°dA)
Yield: 84% (147 mg); White solid, M.p. 151.0–152.0 C, Eluent
1
of the column chromatography: Hexane/EtOAc=2/1; H NMR
(CDCl3): δ 1.24–1.41 (m, 1H, CyH), 1.62–1.84 (m, 7H, CyH),
2.04 (td, J=13.0, 4.9 Hz, 2H, CyH), 5.06 (s, 2H, CH2), 5.11 (s,
1H, OH), 6.93 (d, J=8.6 Hz, 2H, ArH), 7.68 (s, 1H, ArH), 7.97
(d, J=8.6 Hz, 2H, ArH); 13C NMR (CDCl3): δ 22.6 (Cy), 25.1
(Cy), 34.0–34.4 (m, Cy), 69.2 (OÀ CH2), 88.5 (OÀ C), 115.0
(Ar), 115.9 (Cy), 122.0 (q, J=274.6 Hz, CF3), 128.8 (Ar),
130.5 (Ar), 138.3 (Ar), 141.3 (q, J=35.1 Hz, CF3À C), 154.1
(Ar), 155.5 (Ar), 157.4 (Ar); 19F NMR (CDCl3, CFCl3): δ
À 62.24 (s, 3F); IR (KBr) 3338, 2934, 2858, 1608, 1445, 1376,
1223, 1142 cmÀ 1; HRMS (FAB): calcd for [M+H]+
C19H19F3NO2: 350.1368, Found: 350.1377.
Spiro[cyclohexane-1,3’-6’-(2-methylphenyl)-4’-
trifluoromethyl-[1H]-furo[3,4-c]pyridine]°(3hA)
Yield: 65% (110 mg); White solid, M.p. 80.5–81.0 C, Eluent of
1
the column chromatography: Hexane/EtOAc=20/1; H NMR
Spiro[cyclohexane-1,3’-6’-(4-bromophenyl)-4’-
(CDCl3): δ 1.23–1.43 (m, 1H, CyH), 1.62–1.90 (m, 7H, CyH),
2.07 (td, J=12.8, 5.1 Hz, 2H, CyH), 5.08 (s, 2H, CH2), 7.24–
7.48 (m, 5H, ArH); 13C NMR (CDCl3): δ 20.6 (Me), 22.6 (Cy),
25.0 (Cy), 34.0–34.5 (m, Cy), 69.1 (OÀ CH2), 88.5 (OÀ C), 119.7
(Ar), 122.0 (q, J=274.6 Hz, CF3), 126.2 (Ar), 129.0 (Ar),
129.8 (Ar), 131.3 (Ar), 136.6 (Ar), 138.6–138.7 (m, Ar), 140.8
(q, J=35.2 Hz, CF3À C), 153.7 (Ar), 158.5 (Ar); 19F NMR
(CDCl3, CFCl3): δ À 61.99 (s, 3F); IR (KBr) 2972, 2939, 2852,
trifluoromethyl-[1H]-furo[3,4-c]pyridine] (3°eA)
Yield: 89% (183 mg); White solid, M.p. 132.8–133.5 C, Eluent
of the column chromatography: Hexane/EtOAc=20/1; 1H
NMR (CDCl3): δ 1.25–1.43 (m, 1H, CyH), 1.62–1.78 (m, 7H,
CyH), 2.04 (td, J=13.0, 5.0 Hz, 2H, CyH), 5.07 (s, 2H, CH2),
7.60 (d, J=8.6 Hz, 2H, ArH), 7.73 (s, 1H, ArH), 7.92 (d, J=
Adv. Synth. Catal. 2021, 363, 1912–1922
1918
© 2021 Wiley-VCH GmbH