4
Tetrahedron
Commun. 2005, 35, 2723-2728 and references cited therein; (c)
Bovicelli, P.; D’Angelo, V.; Collalto, D.; Verzina, A.; D’Antona,
N.; Lambusta, D. J. Pharm. Pharmacol. 2007, 59 (12), 1697-
1701; (d) Zhou, Z.; Zhao, P.; Huang, W.; Yang, G. Adv. Synth.
Catal. 2006, 348 (1-2), 63-67; (e) Lamba, M.; Makrandi, J. K. J.
Chem. Res.2008, 2008 (4), 225-226.
pyrrolidine and iodine catalysts in DMSO solvent. Several
advantages of this methodology including inexpensive catalysts,
good substrate generality, lack of metal catalysts and products in
high yields with no side reactions make it a useful synthetic
approach to flavones. Also, this method avoids the step of
isolation of chalcone or flavanone intermediates and then
subjecting them to further oxidation.
22. (a) Awuah, E.; Capretta, A. Org. Lett. 2009, 11 (15), 3210-3213;
(b) Lorenz, M.; Kabir, M. S.; Cook, J. M. Tetrahedron Lett. 2010,
51, 1095-1098; (c) Kim, D.; Ham, K.; Hong, S. Org. Biomol.
Chem. 2012, 10, 7305-7312; (d) Kraus, G. A.; Gupta, V. Org.
Lett. 2010, 12 (22), 5278-5280; (e) Kim, K. H.; Lee, H. S.; Kim,
S. H.; Kim, J. N. Tetrahedron Lett. 2012, 53, 2761-2764; (f)
Khoobi, M.; Alipour, M.; Zarei, S.; Jafarpour, F.; Shafiee, A.
Chem. Commun. 2012, 48, 2985-2987; (g) Miao, H.; Yang, Z.
Org. Lett. 2000, 2 (12), 1765-1768; (h) Yang, Q.; Alper, H. J.
Org. Chem. 2010, 75, 948-950; (i) Wu, X-F.; Neumann, H.;
Beller, M. Chem. Eur. J. 2012, 18, 12595-12598; (j) Liang, B.;
Huang, M.; You, Z.; Xiong, Z.; Lu, K.; Fathi, R.; Chen, J.; Yang,
Z. J. Org. Chem. 2005, 70, 6097-6100.
Acknowledgments
M. M. N. thanks CSIR, New Delhi, for awarding Senior
Research Fellowship. Authors also acknowledge CSIR and DST,
New Delhi for financial assistance.
References and notes
23. (a) Sarda, S. R.; Pathan, M. Y.; Paike, V. V.; Pachmase, P. R.;
Jadhav, W. N.; Pawar, R. P. ARKIVOC 2006, (xvi), 43-48 and
references cited therein; (b) Bhosale, R. S.; Sarda, S. R.; Giram, R.
P.; Raut, D. S.; Parwe, S. P.; Ardhapure, S. S.; Pawar, R. P. J.
Iran. Chem. Soc. 2009, 6 (3), 519-522 and references cited
therein; (c) Du, Z.; Ng, H.; Zhang, K.; Zeng, H.; Wang, J. Org.
Biomol. Chem. 2011, 9, 6930-6933.
24. (a) Lee, J. I.; Son, H. S.; Park, H. Bull. Korean Chem. Soc. 2004,
25 (12) 1945-1947; (b) Lee, J. I.; Son, H. S.; Jung, M. G. Bull.
Korean Chem. Soc. 2005, 26 (9) 1461-1463; (c) Nagarathnam, D.;
Cushman, M. J. Org. Chem. 1991, 56 (16), 4884-4887; (d)
Bennardi, D. O.; Romanelli, G. P.; Jios, J. L.; Autino, J. C.;
Baronetti, G. T.; Thomas, H. J. ARKIVOC 2008, (xi), 123-130; (e)
Pérez, M. E.; Ruiz, D. M.; Autino, J. C.; Blanco, M. N.; Pizzio, L.
R.; Romanelli, G. P. J. Porous Mater. 2013, 20, 1433-1440; (f)
Zhao, J.; Zhao, Y.; Fu, H. Org. Lett. 2012, 14 (11), 2710-2713.
25. Maiti, G.; Karmakar, R.; Bhattacharya, R. N.; Kayal, U.
Tetrahedron Lett. 2011, 52, 5610-5612.
1. a) Middleton, E. Jr. Adv Exp Med Biol. 1998, 439, 175-82; (b)
Aherne, S. A.; O’Brien, N. M. Nutrition 2002, 18 (1), 75-81.
2. The Flavonoids, advances in research since 1986; Harborne, J. B.
Ed.; Chapman and Hall: London, 1993.
3. Seijas, J. A.; Va´zquez-Tato, M. P.; Carballido-Reboredo, R. J.
Org. Chem. 2005, 70, 2855-2858 and references cited therein.
4. Verma, A. K.; Pratap, R. Tetrahedron 2012, 68, 8523-8538 and
references cited therein.
5. Orallo, F. Curr. Med. Chem. 2008, 15 (19), 1887-1898.
6. Han, X. H.; Hong, S. S.; Hwang, J. S.; Lee, M. K.; Hwang, B. Y.;
Ro, J. S. Arch. Pharm. Res. 2007, 30 (1), 13-17.
7. Öksüz, S.; Ayyildiz, H.; Johansson, C. J. Nat. Prod. 1984, 47 (5),
902-903.
8. Lin, Y.; Shi, R.; Wang, X.; Shen, H. M. Curr. Cancer Drug
Targets 2008, 8 (7), 634-646.
9. Martens, S.; Mithöfer, A. Phytochemistry 2005, 66, 2399-2407.
10. Gabrielska, J.; Soczyńska-Kordala, M.; Przestalski, S. J. Agric.
Food Chem. 2005, 53, 76-83.
26. Yoshida, M.; Fujino, Y.; Saito, K.; Doi, T. Tetrahedron 2011, 67,
9993-9997.
11. (a) Baker, W. J. Chem. Soc. 1933, 1381-1389; (b) Mahal, H. S.;
Venkataraman, K. J. Chem. Soc. 1934, 1767-1769; (c) Mahal, H.
S.; Venkataraman, K. Curr. Sci. 1933, 4, 214-216; (d) Wheeler, T.
S. Org. Synth. 1952, 32, 72; (e) Wheeler, T. S. Org. Synth. 1963,
4, 478. For recent examples of the Baker–Venkataraman
rearrangement, see: (f) Riva, C.; De Toma, C.; Donadd, L.; Boi,
C.; Pennini, R.; Motta, G.; Leonardi, A. Synthesis 1997, 195-201;
(g) Bois, F.; Beney, C.; Mariotte, A. M.; Boumendjel, A. Synlett
1999, 1480-1482; (h) Ganguly, A. K.; Kaur, S.; Mahata, P. K.;
Biswas, D.; Pramanik, B. N.; Chan, T. M. Tetrahedron Lett. 2005,
46, 4119-4121; (i) Ganguly, A. K.; Mahata, P. K.; Biswas, D.
Tetrahedron Lett. 2006, 47, 1347-1349; (j) Chee, C. F.; Buckle,
M. J. C.; Rahman, N. A. Tetrahedron Lett. 2011, 52, 3120-3123.
12. Allan, J.; Robinson, R. J. Chem. Soc. 1924, 125, 2192-2195.
13. (a) Auwers, K. V.; Markovists, T. Ber. 1908, 41, 2332-2340; (b)
Auwers, K. V.; Pohl, P. Ber. 1915, 48, 85-90; (c) Auwers, K. V.
Ber. 1916, 49, 809-819; (d) Auwers, K. V.; Pohl, P. Liebigs Ann.
Chem. 1914, 405, 243-294.
27. (a) Kumar, P.; Bodas, M. S. Org. Lett. 2000, 2 (24), 3821-3823;
(b) Das, J.; Ghosh, S. Tetrahedron Lett. 2011, 52, 7189-7194.
28. (a) Yakovenko, V. I.; Oganesyan, É. T.; Dorofeenko, G. N. Chem.
Heterocycl. Compd. 1981, 17, 115-118; (b) Golub, A. G.;
Bdzhola, V. G.; Ostrynska, O. V.; Kyshenia, I. V.; Sapelkin, V.
M.; Prykhod’ko, A. O.; Kukharenko, O. P.; Yarmoluk, S. M.
Bioorg. Med. Chem. 2013, 21, 6681-6689.
29. Kavala, V.; Lin, C.; Kuo, C-W.; Fang, H.; Yao, C-F. Tetrahedron
2012, 68 (4), 1321-1329.
30. (a) Kálai, T.; Kulcsar, G.; Osz, E.; Jeko, J.; Sumegi, B., Hidega,
K. ARKIVOC 2004, (vii), 266-276; (b) Zhou, C.; Dubrovsky, A.
V.; Larock, R. C. J. Org. Chem. 2006, 71, 1626-1632; (c) Khilya,
V. P.; Ishchenko, V. V. Chem. Heterocycl. Compd. 2002, 38, 883-
899.
31. Lokhande, P. D.; Sakate, S. S.; Taksande, K. N.; Navghare, B.
Tetrahedron Lett. 2005, 46 (9), 1573-1574.
32. Typical procedure for the synthesis of flavones: 2’-
Hydroxyacetophenone (1 mmol) and substituted aromatic
aldehyde (1 mmol) were mixed together along with pyrrolidine
(0.5 mmol) and iodine (0.05 mmol) in DMSO solvent (10 mL).
The resulting mixture was then heated at 150 oC for the given
time. After completion of reaction (monitored by TLC) the
reaction mass was allowed to cool and diluted with ethyl acetate
(20 mL). Resulting solution was then washed with water and
saturated sodium thiosulphate solution followed by drying over
anhydrous sodium sulphate and concentrating under reduced
pressure to furnish the crude product. The residue obtained was
purified by column chromatography using petroleum ether-ethyl
acetate as an eluent to afford flavones (3a-r).
14. Sashidhara, K. V.; Kumar, M.; Kumar, A. Tetrahedron Lett.
2012, 53, 2355-2359.
15. (a) Venkatesan, P.; Maruthavanan, T. Bull. Chem. Soc. Ethiop.
2011, 25 (3), 419-425; (b) Theja, D. N.; Choudary, T. P.; Reddy,
M. I.; Avsss, G.; Reddy, K. U. Int J Pharm Pharm Sci. 2011, 3
(2), 51-54.
16. Babu, K. R.; Kumar, K. V.; Vijaya, M.; Madhavarao, V.
International Journal Of Pharmacy & Technology 2012, 4 (1),
3943-3950.
17. Sarda, S. R.; Jadhav, W. N.; Pawar, R. P. Int. J. ChemTech Res.
2009, 1 (3), 539-543.
18. Kulkarni, P. S.; Kondhare, D. D.; Varala, R.; Zubaidha, P. K. J.
Serb. Chem. Soc. 2012, 77 (0), 1-12.
19. Ahmed, N.; Ali, H.; Van Lier, J. E. Tetrahedron Lett. 2005, 46,
253-256.
20. (a) Menezes, M. J.; Manjrekar, S.; Pai, V.; Patre, R. E.; Tilve, S.
G. Indian J. Chem. 2009, 48B, 1311-1314; (b) Borse, S. L.; Patel,
M. R.; Borse, L. B. Int. J. Pharm. Res. Dev. 2011, 3 (4), 147-152;
(c) Seijas, J. A.; Va´zquez-Tato, M. P.; Carballido-Reboredo, R. J.
Org. Chem. 2005, 70, 2855-2858; (d) Kabalka, G. W.; Mereddy,
A. R. Tetrahedron Lett. 2005, 46, 6315-6317.
21. (a) Muthukrishnan, M.; Patil, P. S.; More, S. V.; Joshi, R. A.
Mendeleev Commun. 2005, 15 (3), 100-101 and references cited
therein; (b) Singh, O. V.; Muthukrishnan, M.; Raj, G. Synth.
33. 1-(2-Hydroxyphenyl)-3-(pyridin-2-yl)propan-1-one was obtained
when 2-pyridinecarboxaldehyde was subjected to this protocol due
to reduction of the intermediate chalcone by the liberated H2 along
with the corresponding flavanone and flavone.
Supplementary Material
Supplementary material associated with this article can be
found in the online version, at doi: