(Mϩ Ϫ C6H11O, 95%), 153 (70%), 82 (55%); HRMS: found Mϩ,
294.1295. C13H18N4O4 requires 294.1325 (Found: C, 52.88; H,
6.04; N, 18.95. C13H18N4O4 requires C, 53.06; H, 6.12; N,
19.04%).
8-Oxoadenine (38). Mp 301 ЊC (decomposes)(MeOH); νmax
(Nujol)/cmϪ1 1640, 1680, 1695 (–NC᎐O–) 3310 (–NH ); δ (300
᎐
2
H
MHz, DMSO-d6) 8.02 (H-2), 6.22 (–NH2); m/z 152 (Mϩ ϩ 1,
25%), 136 (Mϩ ϩ 1 Ϫ NH2, 100%), 109 (30%), 54 (25%), 44
(50%). The spectral characteristics agreed with the earlier
report for 8-oxoadenine.21
1-(2-Oxopropyl)-3,7-dimethyluric acid (32). Mp 240 ЊC
(CHCl3–MeOH); νmax (Nujol)/cmϪ1 1700 (–C᎐O–), 1640, 1680
᎐
(–NC᎐O–); δ (90 MHz, CDCl ) 2.1 (3H, s, CH CO–), 3.5 (3H,
᎐
H
3
3
Acknowledgements
s, –NCH3), 3.57 (3H, s, –NCH3), 4.7 (2H, s, –NCH2–); δC(75
MHz, CDCl3) 28.0, 30.6, 33.8, 47.8, 98.2, 136.1, 150.0, 153.3,
153.5, 204.0; m/z 252 (Mϩ, 100%), 209 (Mϩ Ϫ CH3CO, 75%),
196 (Mϩ Ϫ C3H5O, 85%); HRMS: found Mϩ, 252.0852.
C10H12N4O4 requires 252.0858.
We thank Professor S. B. Sulia, Department of Microbiology,
Bangalore University, for identifying the strains. Financial
assistance from DBT (New Delhi, India), CSIR (New Delhi,
India) and JNCASR (Bangalore, India) is gratefully acknow-
ledged. Financial support to G. R. S. by the CSIR is greatly
appreciated.
1-Allyl-3,7-dimethyluric acid (33). Mp 305–306 ЊC (CHCl3–
MeOH); νmax (Nujol)/cmϪ1 1640, 1690 (–NC᎐O–); δ (200 MHz,
᎐
H
CDCl3) 3.5 (3H, s, –NCH3), 3.56 (3H, s, –NCH3), 4.59 (2H, td,
References
J 4.5, 13, –N–CH –CH᎐CH ), 5.2 (1H, d, J 10, cis CH᎐CH ),
᎐
᎐
2
2
2
5.3 (1H, d, J 17, trans CH᎐CH ), 5.97 (1H, tdd, J 17, 10.3, 4.5,
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2
CH᎐CH ); δ (22.5 MHz, DMSO-d ) 28.2, 30.9, 42.5, 97.8,
᎐
2
C
6
116.5, 133.0, 136.8, 149.5, 151.8, 152.3; m/z 236 (Mϩ, 100%),
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1-Prop-2-ynyl-3,7-dimethyluric acid (34). Mp 276 ЊC (CHCl3–
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᎐
H
CDCl ) 2.1 (1H, t, J 2.4, HC᎐C–CH ), 3.5 (3H, s, –NCH ), 3.59
᎐
3
2
3
(3H, s, –NCH3), 4.6 (2H, d, J 2.7, –NCH2–); δC(22.5 MHz,
CDCl3) 29.7, 30.3, 34.0, 71.4, 79.1, 97.0, 136.0, 150.7, 153.0,
153.8; m/z 234 (Mϩ, 100%), 153 (25%), 84 (45%), 82 (85%), 67
(57%); HRMS: found Mϩ, 234.0749. C10H10N4O3 requires
234.0752.
1-But-3-enyl-3,7-dimethyluric acid (35). Mp 262 ЊC (CHCl3–
MeOH); νmax (Nujol)/cmϪ1 1640, 1690 (–NC᎐O–); δ (90 MHz,
᎐
H
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᎐
3
2
2
2
3
3.58 (3H, s, –NCH3), 4.0 (2H, t, J 7.2, –N–CH2–CH2), 5.0 (1H,
d, J 10, cis CH᎐CH ), 5.2 (1H, d, J 17, trans CH᎐CH ), 5.8 (1H,
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᎐
᎐
2
2
tdd, J 17, 10.3, 4.5, CH᎐CH ); δ (22.5 MHz, CDCl ) 28.0, 30.7,
᎐
2
C
3
31.8, 40.3, 97.8, 116.6, 135.1, 136.4, 149.5, 151.5, 152.5; m/z 250
(Mϩ, 40%), 196 (Mϩ Ϫ C4H7, 100%), 153 (45%), 82 (50%);
HRMS: found Mϩ, 250.1061. C11H14N4O3 requires 250.1065
(Found: C, 52.73; H, 5.58; N, 22.18. C11H14N4O3 requires C,
52.8; H, 5.6; N, 22.4%).
3-Propyluric acid (36). Mp 279 ЊC (CHCl3–MeOH); νmax
(Nujol)/cmϪ1 1640, 1680 (–NC᎐O–); δ (300 MHz, DMSO-d )
᎐
H
6
0.95 (3H, t, J 6.6, CH3CH2–), 1.64 (2H, m, CH3CH2CH2–), 3.9
(2H, t, J 7.5, –NCH2–), 11.0 (1H, s, –NH); δC(75 MHz,
DMSO-d6) 10.9, 21.5, 44.5, 98.9, 137.7, 151, 153.4, 153.9;
m/z 210 (Mϩ, 100%), 168 (Mϩ Ϫ C3H7, 95%), 137 (Mϩ Ϫ
C2H2NO2, 75%); HRMS: found Mϩ, 210.0748. C8H10N4O3
requires 210.0752.
3-Propyl-1,7-dimethyluric acid (37). Mp 282 ЊC (CHCl3–
MeOH); νmax (Nujol)/cmϪ1 1640, 1680 (–NC᎐O–); δ (90 MHz,
᎐
H
27 C. Wang, J. Wang and C. Chan, Bull. Inst. Chem., Acad. Sin., 1981,
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29 W. Seubert, J. Bacteriol., 1960, 79, 426.
CDCl3) 1 (3H, t, J 7.2, CH3CH2–), 1.6 (2H, m, CH3CH2CH2–),
3.4 (3H, s, –NCH3), 3.5 (3H, s, –NCH3), 3.9 (2H, t, J 7.2,
–NCH2–); δC(75 MHz, CDCl3) 10.8, 21.6, 28, 28.9, 46.0, 99.2,
135.7, 150.0, 153.0, 153.9; m/z 238 (Mϩ, 100%), 196
(Mϩ Ϫ C3H7, 70%), 152 (Mϩ Ϫ C3H4NO2, 50%), 139 (65%);
HRMS: found Mϩ, 238.1059. C10H14N4O3 requires 238.1065.
Paper 9/00089E
680
J. Chem. Soc., Perkin Trans. 1, 1999, 677–680