uncertain, since the aromatization of the pyridine-ring occurred
in the presence of catalytic iodine (20mol%) without oxygen. In
comparison, Wang and co-workers observed that oxygen in air
contributed to the aromatization of the pyridine-ring.
In conclusion, we have developed an interesting domino reac-
tion of diketene, amines, aromatic aldehydes and naphthalenamine
leading to benzo[f ]quinolinyl and benzo[h]quinolinyl acetamides
in the presence of iodine. The mild conditions, the short reaction
time, the operational simplicity and the generality of the reaction
should render this new domino reaction useful for introducing
great molecular diversity. Further studies on the potential uses
of the reaction in synthetic and medicinal chemistry are now in
progress.
128.13, 128.74, 129.18, 129.29, 129.61, 129.90, 129.93, 130.15, 132.81,
133.79, 134.76, 136.02, 139.75, 146.78, 147.60, 151.86, 169.07; MS (ESI+)
m/z 437(M + H); Anal. Calcd for C28H21ClN2O: C, 76.97; H, 4.84; N, 6.41.
Found: C, 76.91; H, 4.87; N, 6.50%.
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Ye. V. Maksakovskaya, I. M. Kulikovskaya, N. R. Dadasheva, M. N.
Lebedeva, A. F. Bekhli, N. D. Lychko and N. A. Uvarova, Med.
Parazitol. Parazit. Bolezni, 1992, 1, 50, (Chem. Abstr., 1992, 117, 251317);
(e) H. R. P. Naik, H. S. B. Naik, T. R. R. Naik, H. R. Naika, K.
Gouthamchandra, R. Mahmood and B. M. K. Ahamed, Eur. J. Med.
Chem., 2009, 44, 981.
Acknowledgements
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Financial support by Nanjing University of Science and Technol-
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Notes and references
‡ Representative procedure for the preparation of compound N-benzyl-2-
(3-(4-chlorophenyl)benzo[f ]quinolin-1-yl)acetamide A1. After a solution
of benzyl amine (2 mmol) and diketene (2 mmol) was stirred in 5 ml
of MeCN at room temperature for 2 h, naphthalene-2-amine (2 mmol)
and 4-chlorobenzaldehyde (2 mmol) were added, the temperature was
increased up to 82 ◦C, and then iodine (0.4 mmol) was added to the
refluxing mixture. 3 min later, yellow precipitates were observed, and
the reaction mixture was solidified in 5 min. The reaction was cooled
to room temperature, and 2 ml of MeCN was added, the precipitates
were isolated by filtration and washing with a solution of sodium
thiosulfate followed by water and EtOH. The yellow product N-benzyl-
2-(3-(4-chlorophenyl)benzo[f ]quinolin-1-yl)acetamide A1 was obtained
after drying in 72% yield (0.63 g), and the purity of the corresponding
product was high: up to 98% based on HPLC analysis. Mp 248–250 ◦C;
1H NMR (500 MHz, DMSO-d6) d 4.35–4.36 (d, CH2, J = 6.00 Hz, 2H),
4.60 (s, CH2, 2H), 7.24–7.30 (m, aromatic, 5H), 7.62–7.74 (m, aromatic,
4H), 7.99–8.01 (d, aromatic, J = 4.00 Hz, 1H), 8.09–8.14 (m, aromatic, 2H),
8.24 (s, CH, 1H), 8.32–8.34 (m, aromatic, 2H), 8.69–8.71 (d, aromatic, J =
5.60 Hz, 1H), 8.82 (s, NH, 1H); 13C NMR (125 MHz, DMSO-d6) d 42.93,
44.92, 124.69, 125.43, 126.02, 126.35, 126.74, 127.31, 127.5, 127.79,128.03,
7 All of the products were new, the copies of 1D NMR for all of
the compounds and the copies of 2D NMR for A3 and B2 see the
supplementary material†.
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