The Journal of Organic Chemistry
Page 16 of 27
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44.9, 36.8, 26.1, 22.6, 20.8; IRv (cm-1): 3449, 3184, 2955, 1619, 1556, 1429, 1299, 778, 741;
HRMS(ESI) calcd for C16H21N2O (M+H)+ 257.1648, found 257.1648.
2-Isopropyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one 2d was synthesized
according to General procedure A from 1d (0.2 mmol, 37.6 mg). The title compound
o
was isolated as a white solid (36.4 mg, 80% yield). mp: 214−217 C; Rf (petroleum
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ether/EtOAc 3:1): 0.3; H NMR (400 MHz, CDCl3) δ 9.37 (brs, 1H), 7.59 (d, J = 8.0 Hz,
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1H), 7.44 (d, J = 8.4, 1H), 7.30 (dd, J = 8.4, 6.8 Hz, 1H), 7.14 (dd, J = 8.0, 7.2 Hz, 1H), 5.05
(hept, J = 6.8 Hz, 1H), 3.61 (t, J = 6.8 Hz, 2H), 3.02 (t, J = 6.8 Hz, 2H), 1.02 (d, J = 6.8 Hz,
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6H); C{1H} NMR (100 MHz, CDCl3) δ 161.1, 137.6, 127.7, 125.0, 124.4, 119.9, 119.8, 117.4,
112.6, 43.2, 40.8, 21.0, 20.0; IRv (cm-1): 3448, 2915, 1636, 1458, 1383, 1129, 1086, 845, 744;
HRMS(ESI) calcd for C14H17N2O (M+H)+ 229.1335, found 229.1335.
2-Benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one 2e was synthesized
according to General procedure A from 1e (0.2 mmol, 50.0 mg). The title compound
o
was isolated as a white solid (40.8 mg, 74% yield). mp: 220−225 C; Rf (petroleum
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ether/EtOAc 4:1): 0.3; H NMR (400 MHz, CDCl3) δ 10.46 (brs, 1H), 7.56 (d, J = 7.6 Hz,
1H), 7.45 (d, J = 8.0 Hz, 1H), 7.39-7.30 (m, 4H), 7.28-7.25 (m, 1H), 7.12 (dd, J = 7.6, 6.8
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Hz, 1H), 4.87 (s, 2H), 3.66 (t, J = 6.8 Hz, 2H), 3.03 (t, J = 6.8 Hz, 2H); C{1H} NMR (100
MHz, CDCl3) δ 161.8, 137.7, 137.6, 128.7, 127.9, 127.5, 126.8, 125.1, 124.7, 120.0, 118.1, 112.7,
49.6, 47.5, 20.7; IRv (cm-1): 3449, 3217, 3027, 1633, 1428, 1327, 1251, 746, 695; HRMS(ESI)
calcd for C18H17N2O (M+H)+ 277.1335, found 277.1337.
2-Allyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one 2f was synthesized according
to General procedure A from 1f (0.2 mmol, 40.0 mg). The title compound was isolated
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as a viscous solid (13.8 mg, 25% yield). Rf (petroleum ether/EtOAc 2:1): 0.3; H NMR
(400 MHz, CDCl3) δ 10.37 (brs, 1H), 7.57 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 8.4 Hz, 1H),
7.30-7.25 (m, 1H), 7.12 (dd, J = 8.4, 6.8 Hz, 1H), 5.95-5.89 (m, 1H), 5.31 (d, J = 17.2 Hz,
1H), 5.25 (d, J = 10.0 Hz, 1H), 4.26 (d, J = 6.0 Hz, 2H), 3.68 (t, J = 7.0 Hz, 2H), 3.07 (t, J =
7.0 Hz, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 161.5, 137.7, 133.4, 127.0, 125.1, 124.6, 119.99,
119.97, 118.1, 117.4, 112.7, 48.6, 47.4, 20.7; HRMS(ESI) calcd for C14H15N2O (M+H)+
227.1179, found 227.1179.
2-Benzyl-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one 2j was synthesized according
to General procedure A from 1j (0.2 mmol, 52.0 mg). The title compound was isolated
as a light yellow solid (49.2 mg, 86% yield). mp: 135−139oC; Rf (petroleum ether/EtOAc
3:1): 0.3; 1H NMR (400 MHz, CDCl3) δ 10.05 (brs, 1H), 7.58 (d, J = 8.0 Hz, 1H), 7.48 (d, J =
8.8 Hz, 1H), 7.30 (dd, J = 8.4, 8.4 Hz, 1H), 7.14 (dd, J = 8.0, 7.2 Hz, 1H), 4.16 (q, J = 7.2
Hz, 2H), 3.89 (t, J = 7.2 Hz, 2H), 3.80 (t, J = 7.2 Hz, 2H), 3.06 (t, J = 7.2 Hz, 2H), 2.76 (t, J
= 6.4 Hz, 2H), 1.26 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ 172.0, 161.8, 137.7,
126.9, 125.1, 124.7, 120.0, 119.9, 118.3, 112.7, 60.7, 49.2, 43.3, 33.4, 20.9, 14.2; HRMS(ESI)
calcd for C16H19N2O3 (M+H)+ 287.1390, found 287.1393.
2-Benzyl-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one 2k was synthesized according
to General procedure A from 1k (0.2 mmol, 51.8 mg). The title compound was isolated
as a viscous solid (43.3 mg, 76% yield). Rf (CH2Cl2/MeOH 20:1): 0.4; 1H NMR (400 MHz,
CDCl3) δ 10.86 (brs, 1H), 7.58 (d, J = 8.0 Hz, 1 H), 7.50 (d, J = 8.0 Hz, 1 H), 7.28 (dd, J =
7.6, 7.2 Hz, 1H), 7.13 (dd, J = 7.6, 7.2 Hz, 1H), 3.94 (t, J = 6.8 Hz, 2H), 3.86 (t, J = 7.2 Hz,
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2H), 3.05 (t, J = 6.8 Hz, 2H), 2.99 (s, 3H), 2.97 (s, 3H), 2.81 (t, J = 6.4 Hz, 2H); C{1H}
NMR (100 MHz, CDCl3) δ 171.1, 162.0, 137.7, 127.0, 125.1, 124.5, 120.0, 119.9, 118.4, 112.6,
49.6, 44.1, 37.3, 35.3, 32.1, 20.8; IRv (cm-1): 3412, 2926, 1628, 1458, 1341, 1156, 1119, 1104, 768,
744; HRMS(ESI) calcd for C16H20N3O2 (M+H)+ 286.1550, found 286.1550.
2,3,4,9-Tetrahydro-6-methyl-2-methyl-1H-Pyrido[3,4-b]indol-1-one
2l
was
synthesized according to General procedure A from 1l (0.2 mmol, 37.8 mg). The title
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