LETTER
An Efficient Synthetic Route to Homocarbonyltopsentine
1535
(8) LaMattina, J. L.; Mularski, C. J. J. Org. Chem. 1986, 51,
413.
(9) Achab, S. Tetrahedron Lett. 1996, 37, 5503; and references
cited therein.
Preparation of derivatives taking advantage of the pres-
ence of iodine on the imidazole ring is currently under
way in our laboratory.
(10) Turner, R. M.; Ley, S. V.; Lindell, S. D. Synlett 1993, 748.
(11) All new compounds gave satisfactory spectroscopic and
analytical data. Selected spectroscopic data: 16: white solid,
mp >210 °C; IR (KBr): 3198, 1609, 1590, 1512, 1415, 1110,
859 cm–1; 1H NMR (300 MHz, DMSO-d6): d 7.22–7.30 (m,
4 H, HAr), 7.53–7.59 (m, 2 H, HAr), 8.02 (s, 1 H, HAr), 8.37–
8.40 (m, 2 H, HAr), 8.97 (s, 1 H, HAr), 9.14 (s, 1 H, HAr),
12.00 (s, 1 H, NH), 12.21 (s, 1 H, NH), 13.70 (s, 1 H, NH);
13C NMR (75 MHz, DMSO-d6): d 112.2 (CH), 112.5 (CH),
113.4 (C), 114.9 (C), 121.6 (CH), 121.7 (2 CH), 122.3 (CH),
122.9 (CH), 123.2 (CH), 124.3 (CH), 126.5 (C), 126.7 (C),
135.7 (CH), 136.2 (C), 136.3 (C), 137.1 (CH), 143.3 (C),
145.5 (C), 176.5 (CO), 181.6 (CO); MS (ESI):
Acknowledgment
This research work was supported by a grant from the Ministère de
la Jeunesse, de l’Education Nationale et de la Recherche to C.M.
References
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m/z 355 (M + H+); HRMS (LSIMS) for C21H15N4O2:
calculated: 355.1195, found: 355.1195. Ia: yellow solid, mp
>210 °C; IR (KBr): 3380, 3200, 1592, 1572, 1525, 1430,
1120, 868 cm–1; 1H NMR (300 MHz, DMSO-d6): d 6.78 (dd,
1 H, J = 1.7 Hz, 8.6 Hz, HAr), 6.92 (br s, 1 H, HAr), 7.20–7.28
(m, 2 H, HAr), 7.53–7.56 (m, 1 H, HAr) 8.01 (s, 1 H, HAr), 8.15
(d, 1 H, J = 8.6 Hz, HAr), 8.38–8.41 (m, 1 H, HAr), 8.96 (br s,
2 H, HAr), 9.33 (s, 1 H, OH), 11.84 (s, 1 H, NH), 11.99 (s, 1
H, NH), 13.63 (s, 1 H, NH); 13C NMR (75 MHz, DMSO-d6):
d 97.6 (CH), 112.2 (CH), 112.3 (CH), 113.6 (C), 114.9 (C),
119.4 (C), 121.7 (CH), 121.8 (CH), 122.1 (CH), 122.9 (CH),
124.2 (CH), 126.8 (C), 135.7 (CH), 135.9 (CH), 136.2 (C),
137.6 (C), 143.3 (C), 145.6 (C), 154.4 (C), 176.3 (CO),
181.6 (CO); MS (ESI): m/z 371 (M + H+); HRMS (LSIMS)
for C21H15N4O3: calculated: 371.1144, found: 371.1143.
(12) Synthesised by formylation (POCl3, DMF)9 and protection
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Synlett 2003, No. 10, 1533–1535 © Thieme Stuttgart · New York