T. Tan et al. / Tetrahedron 61 (2005) 8192–8198
8197
1556, 1509, 1457, 1322, 1260, 1240, 1164, 1040, 963, 747,
673, 610. 1H NMR (200 MHz, CDCl3): d 8.61–6.75 (9H, m,
ArH, H-20), 3.03–3.00 (4H, m, CH2), 2.77–2.72 (4H, m,
CH2), 1.64–1.55 (9H, m, CH3). MS (ESI) m/z: 431.4 (MC).
C26H26ON3Cl (431.95). Anal. Calcd for C26H26ON3Cl: C,
72.29; H, 6.07. Found: C, 72.35; H, 6.13%.
1587, 1508, 1485, 1455, 1302, 1272, 1244, 1163, 1035, 970.
1H NMR (200 MHz, CDCl3): d 8.53–6.53 (10H, m, ArH,
H-20), 3.95–3.93 (2H, m, CH2), 3.75–3.65 (1H, m, CH), 2.73
(3H, s, CH3), 2.15–1.57 (12H, m, CH2), 1.34 (6H, s, CH3),
1.24–1.20 (1H, m, CH). MS (ESI) m/z: 466.33 (MCC1).
C31H35ON3 (465.62). Anal. Calcd for C31H35ON3: C, 79.96;
H, 7.58. Found: C, 79.99; H, 7.61%.
4.3.2. 1,3,3-Trimethyl-60-piperidine-spiro[2,30-[3H]-
naphtho[2,1-b][1,4]oxazine], 2. White solid. Yield 37%.
Mp 226–228 8C. IR: 3069, 1660, 1586, 1486, 1450, 1362,
4.3.8. 5-Chloro-1,3,3-trimethyl-60-decahydro-isoquino-
line-spiro[2,30-[3H]-naphtho[2,1-b][1,4]oxazine], 8.
White solid. Yield 10%. Mp 192–193 8C. IR: 3310, 3030,
1670, 1587, 1571, 1508, 1381, 1358, 1292, 1241, 1164,
1036, 970, 766, 717, 691, 652. 1H NMR (200 MHz, CDCl3):
d 8.52–6.42 (9H, m, ArH, H-20), 3.18–3.12 (2H, m, CH2),
2.83–2.76 (2H, m, CH), 2.70 (3H, CH3), 2.15–1.55 (12H, m,
CH2), 1.32 (6H, s, CH3). MS (ESI) m/z: 500.3 (MC).
C31H34ON3Cl (500.06). Anal. Calcd for C31H34ON3Cl: C,
74.46; H, 6.85. Found: C, 74.50; H, 6.88%.
1
1305, 1276, 1241, 1165, 1030, 967. H 0NMR (200 MHz,
CDCl3): d 8.54–6.56 (10H, m, ArH, H-2 ), 3.01–3.00 (4H,
m, CH2), 2.75 (3H, s, CH3), 1.83–1.80 (4H, m, CH2), 1.83–
1.56 (2H, m, CH2), 1.35 (6H, s, CH3). MS (ESI) m/z: 411.0
(MC). C27H29ON3 (411.53). Anal. Calcd for C27H29ON3: C,
78.80; H, 7.10. Found: C, 78.83; H, 7.13%.
4.3.3. 5-Chloro-1,3,3-trimethyl-60-piperidine-spiro[2,30-
[3H]-naphtha[2,1-b][1,4]oxazine], 3. Colorless prism.
Yield 34%. Mp 230–231 8C. IR: 3030, 1660, 1586, 1566,
1484, 1352, 1241, 1167, 1040, 950, 764, 705, 657. 1H NMR
(200 MHz, CDCl3): d 8.52–6.43 (9H, m, ArH, H-20), 3.00–
2.98 (2H, m, CH2), 2.70 (3H, s, CH3), 1.81–1.76 (4H, m,
CH2), 1.63–1.56 (4H, m, CH3), 1.32 (6H, s, CH3). MS (ESI)
m/z: 445.4 (MC). C27H28ON3Cl (445.97). Anal. Calcd for
C27H28ON3Cl: C, 72.71; H, 6.33. Found: C, 72.75; H,
6.35%.
4.3.9. 5-Chloro-1,3,3-trimethyl-60-hexmethylene-terta-
mino-spiro[2,30-[3H]-naphtho[2,1-b][1,4]oxazine], 9.
White solid. Yield 19%. Mp 226–228 8C. IR: 3030, 1670,
1587, 1571, 1508, 1386, 1281, 1163, 1033, 968, 766, 703,
1
682, 655, 630. H NMR (200 MHz, CDCl3): d 8.52–6.42
(9H, m, ArH, H-20), 3.25–3.20 (4H, m, CH2), 2.70 (3H, s,
CH3), 1.85–1.72 (8H, m, CH2), 1.32 (6H, s, CH3). MS (ESI)
m/z: 460.2 (MC). C28H30ON3Cl (460). Anal. Calcd for
C28H30ON3Cl: C, 73.11; H, 6.57. Found: C, 73.19; H,
6.65%.
4.3.4. 1,3,3-Trimethyl-60-morpholine-spiro[2,30-[3H]-
naphtho[2,1-b][1,4]oxazine], 4. Colorless prism. Yield
40%. Mp 181–183 8C. IR: 3069, 1650, 1588, 1570, 1507,
4.3.10. 1,3,3-Trimethyl-60-dihydro-indolinyl-spiro[2,30-
[3H]-naphtho[2,1-b][1,4]oxazine], 10. Yellow solid.
Yield 29%. Mp 232–234 8C. IR: 3747, 3030, 1670, 1588,
1483, 1363, 1301, 1258, 1164, 1021, 959, 746, 703, 655. 1H
NMR (200 MHz, CDCl3): d 8.62–6.27 (14H, m, ArH, H-20),
3.96–3.91 (2H, m, CH2), 3.18–3.16 (2H, m, CH2), 2.77 (3H,
s, CH3), 1.36 (6H, s, CH3). MS (ESI) m/z: 445.2 (MC).
C30H27ON3 (445.55). Anal. Calcd for C30H27ON3: C, 80.87;
H, 6.11. Found: C, 80.89; H, 6.14%.
1
1486, 1453, 1364, 1300, 1285, 1270, 1240, 1162, 967. H
NMR (200 MHz, CDCl3): d 8.57–6.54 (10H, m, ArH, H-20),
3.95–3.91 (4H, m, CH2), 3.06–3.02 (4H, m, CH2), 2.74 (3H,
s, CH3), 1.34 (6H, s, CH3). MS (ESI) m/z: 414.2 (MCC1).
C26H27O2N3 (413.51). Anal. Calcd for C26H27O2N3: C,
75.52; H, 6.58. Found: C, 75.57; H, 6.63%.
4.3.5. 5-Chloro-1,3,3-trimethyl-60-morpholine-spiro[2,
30-[3H]-naphtho[2,1-b][1,4]oxazine], 5. Colorless plate.
Yield 16%. Mp 204–206 8C. IR: 3072, 1670, 1588, 1569,
1508, 1484, 1417, 1300, 1240, 1162, 1031, 950, 764, 706,
Acknowledgements
1
653, 635, 615. H NMR (200 MHz, CDCl3): d 8.55–6.43
(9H, m, ArH, H-20), 3.95–3.91 (4H, m, CH2), 3.08–3.03
(4H, m, CH2), 2.71 (3H, s, CH3), 1.33 (6H, s, CH3). MS
(ESI) m/z: 448.1 (MC). C26H26O2N3Cl (447.95). Anal.
Calcd for C26H26O2N3Cl: C, 69.71; H, 5.85. Found: C,
69.75; H, 5.89%.
We are grateful to the National Natural Science Foundation
of China for financial supports (Nos. 20490210 and
20372039) and to Prof. Kui-ling Ding for his help (Shanghai
Institute of Organic Chemistry, Chinese Academy of
Sciences).
4.3.6. 1,3,3,5-Tetramethyl-60-decahydro-quinoline-
spiro[2,30-[3H]-naphtho[2,1-b][1,4]oxazine], 6. White
solid. Yield 21%. Mp 184–185 8C. IR: 3354, 3150, 2930,
2853, 2807, 1670, 1586, 1508, 1485, 1455, 1302, 1272,
References and notes
1
1244, 1163, 1036, 969. H NMR (200 MHz, CDCl3): d
8.48–6.48 (9H, m, ArH, H-20), 2.94 (3H, s, CH3), 2.72 (3H,
s, CH3), 1.74–1.57 (12H, m, CH2), 1.30 (6H, s, CH3), 1.18–
1.16 (3H, m, CH2, CH), 0.86–0.81 (1H, m, CH). MS (ESI)
m/z: 480.5 (MCC1). C32H37ON3 (479.65). Anal. Calcd for
C32H37ON3: C, 80.13; H, 7.77. Found: C, 80.16; H, 7.82%.
1. Ciardelli, F.; Fabbri, D.; Pieroni, O.; Fissi, A. J. Am. Chem.
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2. Salemi-Delvaux, C.; Luccioni-Houze, B.; Baillet, G.; Giusti,
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4.3.7. 1,3,3-Trimethyl-60-decahydro-isoquinoline-spiro-
[2,30-[3H]-naphtho[2,1-b][1,4]oxazine], 7. Colorless
plate. Yield 20%. Mp 202–204 8C. IR: 3300, 3051, 1660,
4. Inouye, M.; Ueno, M.; Kitao, T. J. Am. Chem. Soc. 1990, 112,
8977–8979.