January 2012
Facile and Simple Synthesis of Some New Polyfunctionally Heterocyclic
Derivatives Incorporating 2-Imino-2H-chromene Moiety
147
for C39H26N8O2 (638.68): C 73.34, H 4.10, N 17.54%. Found:
C 73.41, H 4.21, N 17.66%.
(s, 1H, naphthyridine), 5.65 (s, 1H, CH-pyrimidine), 6.82–7.81
(m, 21H, ArAH þ NH). MS: m/z 670 (Mþ, 50%). Calcd for
C40H26N6O3S (670.74): C 71.63, H 3.91, N 12.53%. Found: C
71.61, H 4.01, N 12.64%.
6,8-Diamino-7-(benzo[d]thiazol-2-yl)-2-(2-imino-2H-chro-
men-3-yl)-1,4-diphenylpyrido[2,3-c][1,6]naphthyridin-9(1H)-
one (32b). Yellow crystals (MeOH). Yield: 40%. m.p. 156–
158ꢁC. IR: m (cmꢀ1) 1689 (CO), 3282 (NH), 3419, 3495
(NH2). 1H NMR (DMSO): d 4.25 (s, 2H, NH2), 4.47 (s, 2H,
NH2), 6.79–7.32 (m, 20H, ArAH þ NH). MS: m/z 656 (Mþ1,
60%). Calcd for C39H25N7O2S (655.73): C 71.43, H 3.84, N
14.95%. Found: C 71.54, H 3.98, N 15.01%.
REFERENCES AND NOTES
[1] Ellis, G. P. Chromenes, Chromanones, and Chromones.
The Chemistry of Heterocyclic Compounds; Wiley: New York, 1977,
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[2] Bowers, W. S. In Comprehensive Insect Physiology, Bio-
chem Pharmacology; Gilbert, L. I., Kerkut, G. A., Eds.; Pergamon:
Oxford, 1985; Vol. 8, p 551.
6,8-Diamino-1,9-dihydro-2-(2-imino-2H-chromen-3-yl)-9-
oxo-1,4-diphenyl-pyrido[2,3-c][1,6]naphthyridine-7-carboni-
trile (33). It was prepared according to procedure that
described for compound 4. Yellow crystals (MeOH). Yield:
60%. m.p. 188–190ꢁC. IR: m (cmꢀ1) 1690 (CO), 2217 (CN),
3120 (NH), 3432–3490 (NH2). 1H NMR (CDCl3): d 4.12
(s, 2H, NH2), 4.33 (s, 2H, NH2), 4.65 (s, 1H, naphthyridine),
6.79–7.46 (m, 16H, ArAH þ NH). MS: m/z 544 (M-3, 55%).
Calcd for C33H21N7O2 (547.57): C 72.38, H 3.87, N 17.91%.
Found: C 72.49, H 3.99, N 17.99%.
[3] Bowers, W. S.; Ohta, T.; Cleere, J. S.; Marsella, P. A. Sci-
ence 1976, 193, 542.
[4] William, K.; Shailaja, K.; Songchun, J.; Hong, Z.; Jian-
´
ghong, Z.; Shaojuan, J.; Lifen, X.; Candace, C.; Real, D.; Nancy, B.;
Louis, V.; Sylvie, C.; Jennifer, D.; Giorgio, A.; Denis, L.; Serge, L.;
Henriette, G.; Ben, T.; John, D.; Sui, X. C. Bioorg Med Chem Lett
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Myung-Hwa, K.; Chun-Ho, P.; Bo-Young, J.; Tae, G. C.; Hyun-Moo,
C.; Hee-Yoon, L.; Sung, H. H.; Myung, S. K.; Ky-Youb, N.; Gyoon-
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8-(Benzylideneamino)-2-(2-imino-2H-chromen-3-yl)-1,4-
diphenylpyrimido[5,4-c][1,8]naphthyridin-9(1H)-one (34). An
equimolar mixture of 11 (1.2 g, 2 mmol) and benzaldehyde
(0.22 g, 2 mmol) was dissolved in ethanol (30 mL) in the pres-
ence of piperidine (0.2 mL) was refluxed for 6 hours. The
solid product formed after cooling was collected by filtration
and recrystallized from DMF-H2O (3:1) yielded yellow crys-
tals. Yield: 60%. m.p. 284–286ꢁC. IR: m (cmꢀ1) 1695 (CO),
[7] Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew
Chem Int Ed 2000, 39, 734.
[8] Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Angew
Chem Int Ed 2000, 39, 739.
1
3282 (NH). H NMR (DMSO): d 4.69 (s, 1H, naphthyridine),
[9] Maggiani, A.; Tubul, A.; Brun, P. Helv Chim Acta 2000,
83, 650.
4.99 (s, 1H, CH-pyrimidine), 6.21 (s, 1H, -N¼¼CH), 6.93–7.85
(m, 21H, ArAH þ NH). MS: m/z 596 (Mþ, 60%). Calcd for
C38H24N6O2 (596.64): C 76.50, H 4.05, N 14.09%. Found: C
76.58, H 4.17, N 14.21%.
[10] Tadigoppula, N.; Tanvir, K.; Shweta, N.; Neena, G.;
Suman, G. Bioorg Med Chem 2005, 13, 6543.
[11] Cinzia, C.; Nicoletta, D. Bioorg Med Chem 2009, 17, 3720.
[12] Ahmed, M. M.; El-Saghier, M. B.; Naili, B. K.; Rammash,
N. A.; Saleh, Khaled, M. K. Arkivoc 2007, 83.
8-(3-Chloro-2-oxo-4-phenylazetidin-1-yl)-2-(2-imino-2H-
chromen-3-yl)-1,4-diphenylpyrimido[5,4-c][1,8]naphthyridin-
9(1H)-one (36). To a well stirred solution of 34 (1.2 g,
2 mmol) and triethylamine (0.41 mL, 4 mmol) in dry dioxane
(20 mL), chloroacetyl chloride (0.22 mL, 2 mmol) was added
dropwise at room temperature, then the reaction mixture was
refluxed for 8 hours. The precipitate of triethylamine hydro-
chloride was filtered and washed thoroughly with dioxane. The
filtrate was evaporated to one-third of its original volume,
cooled and poured into acidified ice/water and the precipitate
formed washed with water thoroughly, dried and recrystallized
from methanol as brown crystals. Yield: 60%. m.p. 255–
257ꢁC. IR: m (cmꢀ1) 1695–1705 (CO), 3289 (NH). 1H NMR
(DMSO): d 3.92 (d, 1H, azitidene-CH-4), 4.46 (d, 1H, aziti-
dene-CH-3), 4.79 (s, 1H, naphthyridine), 7.11–7.62 (m, 21H,
[13] Laurin, P.; Klich, M.; Dupis-Hamelin, C.; Mauvais, P.; Las-
saigne, P.; Bonnefoy, A.; Musicki, B. Bioorg Med Chem Lett 1999, 9,
2079.
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Ali, Z. E. Turk J Chem 2008, 32, 365.
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S.; Mohan, P. S. I. Euro J Med Chem 2009, 44, 3209.
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mayum, J. S. Euro J Med Chem 2010, 45, 2250.
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bani, O.; Yukio, K.; Akira, H. Bottom of Form Bioorg Med Chem
2010, 18, 2485.
ArAH
C40H25N6O3Cl (673.12): C 71.37, H 3.74, N 12.49, Cl 5.27%.
þ
NH). MS: m/z 673 (Mþ, 55%). Calcd for
[19] Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem Rev
2003, 103, 893.
[20] Nohara, A.; Kuriki, H.; Saijo, T.; Sugihara, H.; Kanno, M.;
Sanno, Y. J Med Chem 1977, 20, 141.
Found: C 71.48, H 3.81, N 12.58, Cl 5.32%.
2-(2-Imino-2H-chromen-3-yl)-8-(4-oxo-2-phenylthiazolidin-
3-yl)-1,4-diphenylpyrimido[5,4-c][1,8]naphthyridin-9(1H)-one
(38). An equimolar mixture of 34 (1.2 g, 2 mmol) and thiogly-
colic acid (0.28 mL, 2 mmol) in dry benzene (20 mL) was
refluxed for 10 hours. The reaction mixture was evaporated to
dryness under reduced pressure. The thiazolidinone was sepa-
rated off, washed with ether and crystallized from ethanolꢀa1s
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Pharm Bull 1974, 22, 2959.
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Tetrahedron 2008, 64, 6607.
yellow crystals. Yield: 60%. m.p. 285–287ꢁC. IR: m (cm
)
1695–1702 (CO), 3289 (NH). 1H NMR (DMSO): d 3.82
(s, 1H, CH-thiazolidine), 4.22 (s, 2H, CH2-thiazolidine), 4.88
[26] Van, H. N.; Bettina, A.; Peter, L. Tetrahedron 2006, 62, 7674.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet