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611
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Ed.; Academic: San Diego, 1999; Vol. 38, pp 219–273.
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Macciantelli, D. J. Chem. Soc., Perkin Trans. 2 1984, 1025.
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Katritzky, A. R., Ed.; Academic: San Diego, 2000; Vol. 76, pp 1–84.
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Chemistry; Katritzky, A. R., Ed.; Academic: San Diego, 2006; Vol. 91, pp 1–134.
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R.; Wawer, I.; Krygowski, T. M.; Mannle, F.; Limbach, H.-H. J. Am. Chem. Soc.
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588.
quinolinyl-1,3-indandione (quinoline yellow) and p-butylaniline in
a similar manner to that described for 2:3: orange solid. Mp 192–
195 ꢁC. 1H NMR (CDCl3):
d
0.96 (t, J¼7.3 Hz, 1H), 1.41 (sextet,
J¼7.3 Hz, 2H), 1.66 (p, J¼7.3 Hz, 2H), 2.67 (dt, J¼7.3 Hz, 2H), 6.49 (d,
J¼7.0 Hz, 1H), 6.76 (d, J¼7.3 Hz, 1H), 6.91 (t, J¼6.8 Hz, 1H), 6.94 (d,
J¼7.6 Hz, 2H), 6.96 (t, J¼7.6 Hz, 1H), 7.18 (d, J¼7.6 Hz, 2H), 7.23 (d,
J¼7.6 Hz, 2H), 7.30 (d, J¼7.6 Hz, 1H), 7.40 (t, J¼7.4 Hz, 1H), 7.58 (t,
J¼7.4 Hz, 1H), 7.71 (d, J¼7.9 Hz, 1H), 7.86 (d, J¼7.9 Hz, 1H), 7.04 (d,
J¼9.0 Hz, 1H), 9.16 (d, J¼9.0 Hz, 1H), 13.85 (br s, 1H). 13C NMR
(CDCl3):
d 14.06, 14.12, 22.25, 22.36, 33.73, 33.96, 35.09, 35.17,
105.29, 118.79, 121.59, 122.97, 124.58, 125.27, 125.51, 126.84, 127.39,
128.75, 128.98, 129.01, 129.05, 132.74, 135.42, 137.19, 137.39, 137.57,
140.68, 145.82, 149.99, 156.44, 157.75, 162.16. MS (m/z) 535 (Mþ),
306,288. Anal. Calcd for C38H37N3. C, 85.20, H; 6.96, N, 7.84. Found:
C, 85.23, H, 6.98, N, 7.58.
The X-ray crystallographic data were collected at cryogenic
temperature (ꢀ50 ꢁC for 1, ꢀ100 ꢁC for (1HD)(ClL), ꢀ180 ꢁC for 2)
on a Rigaku AFC 5S diffractometer, using graphite monochromatised
9. (a) Lycka, A.; Frebort, S.; Almonasy, N. Tetrahedron Lett. 2008, 49, 4213; (b)
Seckarova, P.; Marek, R.; Malinakova, K.; Kolehmainen, E.; Hockova, D.; Hocek,
M.; Sklenari, V. Tetrahedron Lett. 2004, 45, 6259; (c) Siri, O.; Braunstein, P.;
Rohmeer, M.-M.; Benard, M.; Weiter, R. J. Am. Chem. Soc. 2003, 125, 13793; See
also Claramunt, R. M.; Lopez, C.; Maria, M. D. S.; Sanz, D.; Elguero, S. J. Prog.
Nucl. Magn. Spectrosc. 2006, 49, 169.
10. Ferguson, G.; Parvez, M.; Lloyd, D.; Marshall, D.; Potter, D. Acta Crystallogr. 1986,
C42, 912.
11. Coalescence method is applicable to two singlets representing interchange
between two equivalent sites. Therefore, the value estimated herein is an
approximate one.
Mo–K
a
radiation (
l
¼0.71073 Å). Crystal data have been submitted
to CCDC. Crystal data for 1: C23H20N2, P21/c, a¼6.5904(19),
b¼18.541(7), c¼14.561(4),
b
¼90.304(11), V¼1779.2(9) Å3, Z¼4,
Dcalcd¼1.211 g/cm3, R1¼0.0413, wR2¼0.0460, CCDC-7,49,201. Crystal
data for (1HD)(ClL): C23H21N2Cl, P-1, a¼8.576(5), b¼10.508
(6), c¼11.728(6),
a
¼107.06(2),
b
¼102.246(19),
g¼107.83(2), V¼
12. Yavari, I.; Adib, M.; Jahani-Moghaddam, F.; Bijamzadeh, H. R. Tetrahedron 2002,
58, 6901.
907.5(8) Å3, Z¼2, Dcalcd¼1.321 g/cm3, R1¼0.0461, wR2¼0.0830,
CCDC-749202. Crystal data for 2: C28H23N3, Pnma, a¼20.7671(14),
13. Dobosz, R.; Kolehmainen, E.; Valkonen, A.; Osmialowski, B.; Gawinecki, R.
Tetrahedron 2007, 63, 9197.
b¼19.3314(3), c¼5.10301(10), V¼2048.63(15) Å3, Z¼4, Dcalcd
1.302 g/cm3, R1¼0.0432, wR2¼0.0582, CCDC-749203.
¼
14. In 1H NMR, the methylene protons at the
a position of the butyl substituent
appear as a quartet, which is attributed to overlap of two triplets. This means
that the methylene protons adjacent to the benzene ring suffer the most sig-
nificant magnetic nonequivalence among three sets of methylene protons in
the butyl group, in contrast to the 13C NMR signals.
Theoretical calculations have been performed by using Gaussian
03 program package.16 The density functional theory (DFT) was
employed for the full geometric optimizations at the B3LYP/6–
31G(d,p) level.
15. Yavari, I.; Adib, M.; Bijanzadeh, H. R.; Sadegi, M. M. M.; L-Khouzani, H.; Safari, J.
Monatsh. Chem. 2002, 133, 1109.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.;
Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.;
Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.;
Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, H.; Ehara, M.;
Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao,
O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken,
V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A.
J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G.
A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.;
Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Fores-
man, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov,
B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.;
Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.
M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03
Rev.C02; Gaussian,: Wallingford CT, 2004.
Acknowledgements
This work was partially supported by a Grant-in-Aid for Scien-
tific Research (C) from MEXT (No. 21550048).
References and notes
1. Claramunt, R. M.; Elguero, J.; Katritzky, A. R. In Advances in Heterocyclic
Chemistry; Katritzky, A. R., Ed.; Academic: San Diego, 2000; Vol. 77, pp 1–50.
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J. Magn. Reson. 1985, 65, 159; (b) Limbach, H. H.; Wehrle, B.; Zimmermann, H.;