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N,N0-Dipropyl-6-(chloromethyl)±2-oxo-2H-1-benzopyran-
3-carboxamide (23). This was prepared according to the
general procedure (yield: 41%): mp 118±124 ꢀC (ethyl
acetate:petroleum ether 40±60 ꢀC); IR 3045 (C±H
7.10±7.35 (m, 2H, 8-H, 50-H), 7.55 (s, 1H, 5-H), 7.60 (d,
1H, 7-H), 8.60 (s, 1H, 4-H). Anal. (C18H13O5Cl) C, H.
3-Fluorophenyl 6-(chloromethyl)-2-oxo-2H-1-benzopyran-
3-carboxylate (29). This was prepared according to the
general procedure (yield: 52%): mp 195±197 ꢀC (aceto-
nitrile); IR 3070 (C±H arom), 1774 (CO ester), 1756
arom), 2970, 2932, 2873 (C±H aliph), 1715 (CO lac-
1
tone), 1631 (CO amide) cm
;
1H NMR (80 MHz,
CDCl3, HMDS), d 0.70 (m, 6H, 2* CH3), 1.55 (m, 4H,
2* CH2-CH2-CH3), 3.10 (t, 2H, N-CH2 aCH2CH3), 3.40
(t, 2H, N-CH2 bCH2CH3), 4.55 (s, 2H, CH2Cl), 7.25 (d,
1H, 8-H), 7.45 (s, 1H, 5-H), 7.50 (d, 1H, 7-H), 7.65 (s,
1H, 4-H). Anal. (C17H20NO3Cl) C, H, N.
(CO lactone), 1709, 1622, 1609, 1573, 1486, 1444,
1
1380, 1240, 1223 cm
;
1H NMR (80 MHz, CDCl3,
HMDS), d 4.55 (s, 2H, CH2Cl), 6.90±7.35 (m, 5H,
C6H4, 8-H), 7.60 (s, 1H, 5-H), 7.65 (d, 1H, 7-H), 8.60 (s,
1H, 4-H). Anal. (C17H10O4FCl) C, H.
6-(Chloromethyl)-2-oxo-3-piperidinocarbonyl-2H-1-benzo-
pyran-3-carboxamide (24). This was prepared according
to the general procedure (yield: 34%): mp 153±155 ꢀC
(ethyl acetate:petroleum ether 40±60 ꢀC); IR 3044 (C±H
3-Bromophenyl 6-(chloromethyl)-2-oxo-2H-1-benzopyran-
3-carboxylate (30). This was prepared according to the
general procedure (yield: 37%): mp 177±178 ꢀC (aceto-
nitrile), IR 3086 (C±H arom), 3062 (C±H arom), 1771
(CO ester), 1724 (CO lactone), 1619, 1574, 1468,
arom), 2944, 2856 (C±H aliph), 1714 (CO lactone),
1
1640 (CO amide), 1580, 1445, 1255, 1237, 1178 cm
;
1H NMR (400 MHz, CDCl3, TMS), d 1.60±1.68 (m, 6H,
(CH2CH2)2CH2), 3.30±3.71 (m, 4H, (CH2CH2)2), 4.63
(s, 2H, CH2Cl), 7.35 (d, 1H, 8-H), 7.55 (s, 1H, 5-H), 7.59
(d, 1H, 7-H), 7.83 (s, 1H, 4-H). Anal. (C16H16NO3Cl) C,
H, N.
1375, 1244 cm 1; H NMR (80 MHz, CDCl3, HMDS),
1
d 4.55 (s, 2H, CH2Cl), 7.05±7.40 (m, 5H, C6H4, 8-H),
7.60±7.70 (s+d, 2H, 5-H, 7-H), 8.60 (s, 1H, 4-H). Anal.
(C17H10O4BrCl) C, H.
3-Chloro-5-methoxyphenyl 6-(chloromethyl)-2-oxo-2H-1-
benzopyran-3-carboxylate (32). This was prepared
according to the general procedure (yield: 50%): mp 184±
185 ꢀC (acetonitrile); IR 3064 (C±H arom), 1779 (CO
ester), 1758 (CO lactone), 1621, 1573, 1377, 1242,
1222, 1150 cm 1; 1H NMR (80 MHz, CDCl3, HMDS), d
3.70 (s, 3H, OCH3), 4.55 (s, 2H, CH2Cl), 6.60±6.90 (m,
3H, C6H3), 7.30 (d, 1H, 8-H), 7.60 (s, 1H, 5-H), 765 (d,
1H, 7-H), 8.60 (s, 1H, 4-H). Anal. (C18H12O5Cl2) C, H.
6-(Chloromethyl)-3-morpholinocarbonyl-2-oxo-2H-1-ben-
zopyran-3-carboxamide (25). This was prepared according
to the general procedure (yield: 37%): mp 210±212 ꢀC
(ethyl acetate:petroleum ether 40±60 ꢀC); IR 3044, 3027
(C±H arom), 2992, 2922, 2858 (C±H aliph), 1718 (CO
lactone), 1626 (CO amide), 1582, 1469, 1275, 1248,
1178 cm 1; 1H NMR (400 MHz, CDCl3, TMS), d 3.39±
3.80 (m, 8H, (CH2CH2)2), 4.64 (s, 2H, CH2Cl), 7.37 (d,
1H, 8-H), 7.57 (s, 1H, 5-H), 7.62 (d, 1H, 7-H), 7.94 (s,
1H, 4-H). Anal. (C15H14NO4Cl) C, H, N.
2,3-Dichlorophenyl 6-(chloromethyl)-2-oxo-2H-1-benzo-
pyran-3-carboxylate (33). This was prepared according
to the general procedure (yield: 34%): mp 173±174 ꢀC
(ethyl acetate); IR 3051 (C±H arom), 1771 (CO ester),
1723 (CO lactone), 1620, 1572, 1450, 1433, 1374, 1238,
2-Nitrophenyl 6-(chloromethyl)-2-oxo-2H-1-benzopyran-
3-carboxylate (26). This was prepared according to the
general procedure (yield: 37%): mp 163±164 ꢀC (aceto-
nitrile); IR 3077 (C±H arom), 1768 (CO ester), 1727
(CO lactone), 1609, 1576, 1548, 1374, 1349, 1242, 1204
cm 1; 1H NMR (400 MHz, CDCl3, TMS), d 4.67 (s, 2H,
CH2Cl), 7.41±7.51 (m, 3H, 8-H, 40-H, 60-H), 7.72±7.77
(m, 3H, 5-H, 7-H, 50-H), 8.18 (dd, 1H, 30-H), 8.79 (s,
1H, 4-H). Anal. (C17H10NO6Cl) C, H, N.
1
1215 cm 1; H NMR (400 MHz, CDCl3, TMS), d 4.66
(s, 2H, CH2Cl), 7.25±7.31 (m, 2H, 50-H, 60-H), 7.41±7.44
(m, 2H, 8-H, 40-H), 7.72±7.74 (s+d, 2H, 5-H, 7-H), 8.80
(s, 1H, 4-H). Anal. (C17H9O4Cl3) C, H.
2,5-Dichlorophenyl 6-(chloromethyl)-2-oxo-2H-1-benzo-
pyran-3-carboxylate (34). This was prepared according
to the general procedure (yield: 40%): mp 197±199 ꢀC
(ethyl acetate); IR 3092, 3045 (C±H arom), 1769 (CO
ester), 1721 (CO lactone), 1621, 1573, 1474, 1372,
3-Tri¯uoromethylphenyl 6-(chloromethyl)-2-oxo-2H-1-
benzopyran-3-carboxylate (27). This was prepared
according to the general procedure (yield: 46%): mp
162±163 ꢀC (acetonitrile); IR 3069 (C±H arom), 1772
1
1241, 1220 cm 1; H NMR (400 MHz, CDCl3, TMS),
(CO ester), 1756 (CO lactone), 1621, 1574, 1336,
d 4.66 (s, 2H, CH2Cl), 7.25 (d, 1H, 40-H), 7.35 (d, 1H,
60-H), 7.41±7.44 (m, 2H, 8-H, 30-H), 7.72±7.74 (s+d,
2H, 5-H, 7-H), 8.79 (s, 1H, 4-H). Anal. (C17H9O4Cl3) C,
H.
1
1239, 1223, 1200 cm
;
1H NMR (80 MHz, CDCl3,
HMDS), d 4.55 (s, 2H, CH2Cl), 7.15±7.40 (m, 5H,
C6H4, 8-H), 7.55 (s, 1H, 5-H), 7.60 (d, 1H, 7-H), 8.65 (s,
1H, 4-H). Anal. (C18H10O4F3Cl) C, H.
2,6-Dichlorophenyl 6-(chloromethyl)-2-oxo-2H-1-benzo-
pyran-3-carboxylate (35). This was prepared according
to the general procedure (yield: 43%): mp 177±178 ꢀC
(ethyl acetate); IR 3074 (C±H arom), 1773 (CO ester),
1720 (CO lactone), 1619, 1571, 1488, 1450, 1376, 1228
cm 1; 1H NMR (400 MHz, CDCl3, TMS), d 4.66 (s, 2H,
CH2Cl), 7.22 (dd, 1H, 40-H), 7.40±7.43 (m, 3H, 8-H, 30-
H, 50-H), 7.72±7.74 (s+d, 2H, 5-H, 7-H), 8.55 (s, 1H, 4-
H). Anal. (C17H9O4Cl3) C, H.
3-Methoxyphenyl 6-(chloromethyl)-2-oxo-2H-1-benzo-
pyran-3-carboxylate (28). This was prepared according
to the general procedure (yield: 47%): mp 133±135 ꢀC
(CHCl3:petroleum ether 40±60 ꢀC); IR 3063 (C±H
arom), 1775 (CO ester), 1757 (CO lactone), 1622,
1
1609, 1574, 1489, 1377, 1245, 1224, 1147 cm
;
1H
NMR (80 MHz, CDCl3, HMDS), d 3.70 (s, 3H, OCH3),
4.55 (s, 2H, CH2Cl), 6.7±6.8 (m, 3H, 20-H, 40-H, 60-H),