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N. Thota et al. / Bioorg. Med. Chem. 16 (2008) 6535–6543
4.2.11. Preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid
isopropyl amide (12)
(1H, br s, CH2CH@), 5.78 (1H, d, J = 10.3 Hz, CHCH@CHCO), 6.11
(1H, d, J = 15.0 Hz, CH@CHCO), 7.53 (1H, dd, J = 10.3 and 15.0 Hz,
CHCH@CHCO).
This was prepared in 90% yield from 2 by the procedure as de-
scribed for compound 3. Anal. Calcd for C15H25NO: C, 76.55; H,
10.71; N, 5.95%. Found: C, 76.87; H, 10.73; N, 5.99%. MS (%) M+ at
m/z 235 (40), 180 (100), 179 (35), 166 (54), 152 (36) 151 (33),
136 (28), 96 (11), 82 (15), 68 (88). IR (neat). 3332, 2966, 2930,
4.2.16. Preparation of 5,9-dimethyl-deca-2,8-dienoic acid (2a)
This was prepared in 88% yield from 1a by the procedure as de-
scribed for compound 2. Anal. Calcd for C12H20O2: C, 73.43; H,
10.27%. Found: C, 73.46; H, 10.30%. MS (%) M+ at m/z 196 (30),
152 (52), 126 (46), 112 (75), 83 (54), 69 (100). IR (neat). 2961,
2877, 1652, 1541, 1458, 1382, 1282, 1092, 1019, 671, 615 cmÀ1
.
1H NMR major isomer: d 1.30 (6H, d, J = 6.5 Hz, –NHCH(CH3)2),
1.62 and 1.67 (3H each, s, @C(CH3)2), 1.88 (3H, s, @CCH3), 2.15
(4H, br s, 2Â CH2), 4.01 (1H, m, –NHCH), 4.98 (1H, br s, CH2CH@),
5.89–6.05 (2H, m, CHCH@CHCO), 7.48 (1H, dd, J = 11.5 and
14.9 Hz, CHCH@CHCO).
2922, 1701, 1651, 1419, 1379, 1282, 1093, 984, 939, 686 cmÀ1
.
1H NMR major isomer: d 0.93 (3H, d, J = 6.8 Hz, CHCH3), 1.08–
1.17 (3H, m, CH3CHCH2), 1.58 and 1.64 (3H each, s, @C(CH3)2),
1.94–2.29 (4H, m, CH2CHCH2), 5.08 (1H, br s, CH2CH@), 5.82 (1H,
d, J = 15.5 Hz, CH@CHCO), 6.99–7.14 (1H, m, CH@CHCO). The ethyl
4.2.12. Preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid
o-toluidine (13)
ester of 2a was prepared in 92% yield as per literature method30
.
Anal. Calcd for C14H24O2: C, 74.95; H, 10.78%. Found: C, 74.98; H,
10.81%. MS (%) M+ at m/z 224 (82), 193 (27), 188 (17), 161 (100),
117 (27), 106 (25), (51). IR (neat). 3386, 2962, 2924, 1720, 1652,
This was prepared in 90% yield from 2 by the procedure as de-
scribed for compound 3. Anal. Calcd for C19H25NO: C, 80.52; H,
8.89; N, 4.94%. Found: C, 80.66; H, 8.91; N, 4.93%. MS (%) M+ at
m/z 283 (30), 198 (100), 191 (17), 190 (27), 177 (80), 166 (59),
160 (91), 138 (67), 107 (53), 93 (30), 92 (7), 83 (59), 69 (80), 55
(43). IR (neat). 3317, 2926, 2855, 1715, 1604, 1511, 1383, 1244,
1437, 1378, 1310, 1266, 1182, 1119, 1045, 695, 541 cmÀ1 1H
.
NMR major isomer: d 0.95 (3H, d, J = 6.6 Hz, CHCH3), 1.09–1.13
(6H, m, CH3CHCH2 and OCH2CH3), 1.60 and 1.69 (3H each, s,
@C(CH3)2), 1.96–2.25 (4H, m, CH2CHCH2), 4.19 (2H, q, OCH2), 5.08
(1H, br s, CH2CH@), 5.82 (1H, d, J = 15.5 Hz, CH@CHCO), 6.94–
6.99 (1H, m, CH@CHCO).
1073, 1035, 829 cmÀ1 1H NMR major isomer: d 1.60 and 1.68
.
(3H each, s, @C(CH3)2), 1.89 (3H, s, @CCH3), 2.15 (4H, br s, 2Â
CH2), 2.29 (3H, s, Ar-CH3), 5.09 (1H, br s, CH2CH@), 5.82–6.03
(2H, m, CHCH@CHCO), 7.03–7.22 (4H, m, Ar-H), 7.59 (1H, dd,
J = 11.6 and 15.2 Hz, CHCH@CHCO).
4.2.17. Preparation of 5,9-dimethyl-deca-2,8-dienoic acid
piperidide (17)
This was prepared in 87% yield from 2a by the procedure as de-
scribed for compound 3. Anal. Calcd for C17H29NO: C, 77.51; H,
11.10; N, 5.32%. Found: C, 77.53; H, 11.16; N, 5.38%. MS (%) M+1
at m/z M++1 264 (100), 248 (35), 208 (20), 195 (18), 181 (25),
180 (40), 114 (20), 111 (18), 86 (35), 84 (76). IR (neat). 2928,
4.2.13. Preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid
morpholide (14)
This was prepared in 90% yield from 2 by the procedure as de-
scribed for compound 3. Anal. Calcd for C16H25NO2: C, 72.96; H,
9.57; N, 5.32%. Found: C, 72.97; H, 9.56; N, 5.34%. MS (%) M+ at
m/z 263 (30), 208 (54), 190 (34), 148 (41), 133 (14), 120 (63),
119 (38), 115 (61), 107 (76), 101 (92), 100 (100), 95 (14). IR (neat).
2855, 1656, 1620, 1440, 1253, 1220, 1137, 1015, 852, 554 cmÀ1
.
1H NMR major isomer: d 0.94 (3H, d, J = 6.9 Hz, CHCH3), 1.08–
1.16 (3H, m, CH3CHCH2), 1.25–1.70 (12H, m, @C(CH3)2 and –N–
CH2(CH2)3), 1.96–2.25 (4H, m, CH2CHCH2), 3.48–3.57 (4H, m, 4.19
–N(CH2)2), 5.08 (1H, br s, CH2CH@), 6.26 (1H, d, J = 15.0 Hz,
CH@CHCO), 6.76–6.84 (1H, m, CH@CHCO).
3386, 2927, 2857, 1643, 1439, 1378, 1115, 760 cmÀ1 1H NMR ma-
.
jor isomer: d 1.61 and 1.67 (3H each, s, @C(CH3)2), 1.89 (3H, s,
@CCH3), 2.12 (4H, br s, 2Â CH2), 3.35 (4H, br s, –N–(CH2)2), 3.65
(4H, br s, –O–(CH2)2), 5.10 (1H, br s, CH2CH@), 6.09 (1H, d,
J = 11.7 Hz, CHCH@CHCO), 6.42 (1H, d, J = 14.6 Hz, CH@CHCO),
7.56 (1H, dd, J = 11.7 and 14.6 Hz, CHCH@CHCO).
4.2.18. Preparation of 5,9-dimethyl-deca-2,8-dienoic acid
benzyl amide (18)
This was prepared in 92% yield from 2a by the procedure as
described for compound 3. Anal. Calcd for C19H27NO: C, 79.95;
H, 9.53; N, 4.91. Found: C, 80.00; H, 9.56; N, 4.95. MS (%) M+ at
m/z 285 (12), 270 (28), 242 (46), 151 (75), 108 (100), 80 (20). IR
(neat). 3292, 3065, 2923, 2853, 1666, 1632, 1547, 1454, 1376,
4.2.14. Preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid
isobutyl amide (15)32
This was prepared in 72% yield from 2 by the procedure as de-
scribed for compound 3. Anal. Calcd for C16H27NO: C, 70.06; H,
10.91; N, 5.62%. Found: C, 72.07; H, 10.92; N, 5.29%. MS (%) M+ at
m/z 249 (75), 234 (60), 206 (25), 191 (100), 162 (70), 129 (80),
93 (95), 53 (70). IR (neat). 3312, 2925, 2854, 1718, 1655, 1544,
1240, 1095, 985, 741, 697 cmÀ1 1H NMR major isomer: d 0.92
.
(3H, d, J = 6.6 Hz, CHCH3), 1.19–1.35 (3H, m, CH3CHCH2), 1.57
and 1.66 (3H each, s, @C(CH3)2), 1.98–2.08 (4H, m, CH2CHCH2),
4.42 (2H, s, –NHCH2), 4.89 (1H, br s, CH2CH@), 5.99 (1H, d,
J = 15.13 Hz, CH@CHCO), 6.76–6.84 (1H, m, CH@CHCO), 7.20–
7.13 (5H, m, 5Â Ar-H).
1384, 1279, 1073, 981, 813 cmÀ1 1H NMR major isomer: d 0.84
.
(6H, d, J = 5.5 Hz, CH(CH3)2), 1.61 and 1.68 (3H each, s, @C(CH3)2),
1.71, (1H, m, CH(CH3)2), 1.85 (3H, s, @CCH3), 2.08 (4H, br s, 2Â
CH2), 3.17 (2H, t, J = 6.4 Hz, –NH–CH2), 5.06 (1H, br s, CH2CH@),
5.75 (1H, d, J = 10.2 Hz, CHCH@CHCO), 6.08 (1H, d, J = 14.9 Hz,
CH@CHCO), 7.51 (1H, dd, J = 10.2 and 14.9 Hz, CHCH@CHCO).
4.2.19. Preparation of 5,9-dimethyl-deca-2,8-dienoic acid
n-octylamide (19)
This was prepared in 87% yield from 2a by the procedure as de-
scribed for compound 3. Anal. Calcd for C20H37NO: C, 78.11; H,
12.13; N, 4.55%. Found: C, 78.19; H, 12.16; N, 4.58%. MS (%) M+
at m/z M+ 307 (32), 265 (17), 224 (100), 206 (8), 181 (10), 156
(41), 141 (5), 132 (8), 94 (70). IR (neat). 3292, 2957, 2925, 2855,
4.2.15. Preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid
diisopropylamide (16)
This was prepared in 96% yield from 2 by the same procedure as
described for compound 3. Anal. Calcd for C18H31NO: C, 77.92; H,
11.26; N, 5.05%. Found: C, 77.00; H, 11.29; N, 5.10%. MS (%) M+ at
m/z 277 (35), 234 (60), 191 (15), 176 (55), 148 (15), 122 (100),
107 (25), 92 (15). IR (neat). 2922, 2852, 1648, 1453, 1378, 1265,
1666, 1629, 1549, 1458, 1377, 1169, 980, 840, 722 cmÀ1 1H NMR
.
major isomer: d 0.91–0.97 (6H, m, CHCH3 and CH2CH3), 1.18–
1.26 (13H, m, CH3CHCH2 and –NHCH2CH2(CH2)5), 1.38–1.41 (2H,
m, –NHCH2CH2), 1.57 and 1.67 (3H each, s, @C(CH3)2), 1.97–2.18
(4H, m, CH2CHCH2), 3.29 (2H, m, –NHCH2), 5.15 (1H, br s, CH2CH@),
5.74 (1H, d, J = 15.2 Hz, CH@CHCO), 6.72–6.87 (1H, m, CH@CHCO).
1087, 821 cmÀ1
.
1H NMR major isomer: d 0.81 (12H, d, 2Â
CH(CH3)2), 1.64 and 1.71 (3H each, s, @C(CH3)2), 1.83 (3H, s,
@CCH3), 2.25 (4H, br s, 2Â CH2), 4.12 (2H, m, 2Â CH(CH3)2), 5.08