ꢀ
A. Juranovic et al. / Tetrahedron 67 (2011) 3490e3500
3499
64.42; H, 4.73; N, 9.39%]; nmax (KBr) 3341, 1664, 1601, 1531, 1522,
1343 cmꢁ1
dH (300 MHz, CDCl3) 2.52 (3H, s, Me), 2.61 (3H, s, Me),
2-H), 9.81 (1H, s, NH); dC (75.5 MHz, DMSO-d6) 17.7, 20.4, 24.6, 29.3,
39.6, 120.0, 122.0, 131.4, 131.9, 137.2, 137.4, 173.0, 201.0; m/z (ESþ)
254 (MNaþ), 232 (MHþ).
;
7.28 (1H, d, J 8.2 Hz, 5-H), 7.57 (1H, dd, J 8.2, 2.3 Hz, 6-H), 7.88 (1H,
br s, NH), 8.05 and 8.36 (2H each, AA0XX0, J 8.7 Hz, C6H4NO2), 8.09
(1H, d, J 2.2 Hz, 2-H); dC (75.5 MHz, CDCl3) 21.0, 29.6, 121.2, 123.2,
124.0, 128.3, 132.7, 135.06, 135.08, 138.4, 140.2, 149.8, 163.8, 201.4;
m/z (ESþ) 321 (MNaþ), 299 (MHþ).
4.4.11. N-(3-Acetyl-4-methylphenyl)cyclopropanecarboxamide (5k).
Me
4.4.8. N-(3-Acetyl-4-methylphenyl)-6-chloronicotinamide (5h).
MeOC
NH
Me
5k
O
Me OC
NH
Yield: 140 mg (65%) as a pale yellow solid, mp 85e88 ꢀC (EtOH);
nmax (KBr) 3279, 1682, 1651, 1528, 1437, 1409 cmꢁ1
dH (300 MHz,
5h
O
N
;
DMSO-d6) 0.81 (4H, m, 2ꢂ CH2), 1.77 (1H, m, 10-H), 2.37 (3H, s, Me),
2.51 (3H, s, Me), 7.20 (1H, d, J 8.3 Hz, 5-H), 7.62 (1H, dd, J 8.3, 2.2 Hz,
6-H), 8.05 (1H, d, J 2.2 Hz, 2-H), 10.28 (1H, s, NH); dC (75.5 MHz,
DMSO-d6) 7.1, 14.5, 20.3, 29.3, 119.8, 121.9, 131.3, 131.9, 137.2, 137.5,
171.7, 201.1; m/z (ESþ) 240 (MNaþ), 218 (MHþ); HRMS (ESþ): MHþ,
found 218.1179. C13H16NO2 requires 218.1181.
Cl
Yield: 213 mg (74%) as an orange solid, mp 141e144 ꢀC (EtOH/
H2O); [Found: C, 62.34; H, 4.53; N, 9.40. C15H13ClN2O2 requires C,
62.40; H, 4.54; N, 9.70%]; nmax (KBr) 3356, 1701, 1672, 1589, 1532,
1497 cmꢁ1
; dH (300 MHz, DMSO-d6) 2.42 (3H, s, Me), 2.56 (3H, s,
Me), 7.29 (1H, d, J 8.2 Hz, 5-H), 7.71 (1H, d, J 8.4 Hz, 50-H), 7.84 (1H,
dd, J 8.2, 2.2 Hz, 6-H), 8.19 (1H, d, J 2.2 Hz, 2-H), 8.37 (1H, dd, J 8.4,
2.2 Hz, 40-H), 8.97 (1H, dd, J 2.2 Hz, 20-H), 10.56 (1H, s, NH); dC
(75.5 MHz, DMSO-d6) 20.4, 29.4, 121.3, 123.3, 124.1, 129.6, 132.0,
132.7, 136.5, 137.5, 138.9, 149.2, 152.8, 162.8, 200.9; m/z (ESþ) 311
(MNaþ), 289 (MHþ).
Acknowledgements
We thank the Ministry of Higher Education, Science and
Technology of the Republic of Slovenia and the Slovenian Re-
search Agency for financial support (P1-0230-0103 and P1-0175).
Dr. B. Kralj and Dr. D. Zigon (Center for Mass Spectroscopy, ‘Jozef
Stefan’ Institute, Ljubljana, Slovenia) are gratefully acknowledged
for the mass measurements. This work was also partially sup-
ported with infrastructure of EN/FIST Center of Excellence,
Ljubljana, and computational facilities of the National Institute of
Chemistry, Ljubljana (Slovenia).
ꢀ
ꢀ
4.4.9. Ethyl 5-(benzoylamino)-2-[(ethoxycarbonyl)methyl]benzoate
(5i)5.
CO2Et
Supplementary data
EtO2C
NHCOPh
5i
Supplementary data associated with this article can be found in
Yield: 259 mg (73%) as a pale yellow solid, lit.5 mp 170.5e171.5 ꢀC
(MeOH); mp 170.5e171.5 ꢀC (MeOH); [Found: C, 67.36; H, 6.21; N,
4.00. C20H21NO5 requires C, 67.59; H, 5.96; N, 3.94%]; nmax (KBr)
References and notes
3298, 1736, 1714, 1651, 1588, 1523, 1420 cmꢁ1
; dH (300 MHz, CDCl3)
1. Nicolau, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem.,
Int. Ed. 2002, 41, 1668e1698.
1.25 (3H, t, J 7.1 Hz, CH2CH3),1.37 (3H, t, J 7.1 Hz, CH2CH3), 3.99 (2H, s,
CH2), 4.15 (2H, q, J 7.1 Hz, CH2CH3), 4.32 (2H, q, J 7.1 Hz, CH2CH3), 7.24
(1H, d, J 8.9 Hz, 3-H), 7.53 (3H, m, Ph), 7.88 (2H, m, Ph), 7.95 (1H, dd,
J 8.9, 2.4 Hz, 4-H), 7.98 (1H, br s, NH), 8.10 (1H, d, J 2.4 Hz, 6-H); dC
(75.5 MHz, CDCl3) 14.2, 40.2, 60.8, 61.1, 122.4, 123.8, 127.1, 128.8,
130.5, 131.7, 132.0, 132.9, 134.6, 137.2, 165.7, 166.6, 171.7 (1 signal
hidden); m/z (EI) 355 (7, Mþ), 105 (100%).
2. (a) Ellis, G. P. In Comprehensive Heterocyclic Chemistry: Pyrans and Fused Pyrans:
(ii) Reactivity; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 3,
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4.4.10. N-(3-Acetyl-4-methylphenyl)cyclobutanecarboxamide (5j).
Me
MeOC
NH
5j
O
Yield: 146 mg (63%) as a pale yellow solid, mp 67e70 ꢀC (EtOH);
ꢀ
ꢀ
Pozgan, F.; Kocevar, M. Heterocycles 2009, 77, 657e678.
[Found: C, 72.44; H, 7.43; N, 5.97. C14H17NO2 requires C, 72.70; H,
3. (a) Shusherina, N. P. Russ. Chem. Rev. 1974, 43, 1771e1793; (b) Afarinkia, K.;
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Greenwich, 1999; pp 47e83; (d) Tolmachova, N. A.; Gerus, I. I.; Vdovenko, S. I.;
7.41; N, 6.06%]; nmax (KBr) 3266, 1686, 1657, 1610, 1524, 1493 cmꢁ1
;
dH (300 MHz, DMSO-d6) 1.89 (2H, m, 3-CH2), 2.19 (4H, m, 2-CH2, 4-
CH2), 2.37 (3H, s, Me), 2.51 (3H, s, Me), 3.22 (1H, m, 10-H), 7.20 (1H,
d, J 8.3 Hz, 5-H), 7.66 (1H, dd, J 8.3, 2.3 Hz, 6-H), 8.06 (1H, d, J 2.3 Hz,
€
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