European Journal of Chemistry

3-Formylchromones as diverse building blocks in heterocycles synthesis



Main Article Content

Tarik El-Sayed Ali
Magdy Ahmed Ibrahim
Nasser Mohamed El-Gohary
Azza Mohamed El‐Kazak

Abstract

This review covers the chemical reactivity of 3-formylchromones towards condensation reactions with a variety of carbon and nitrogen nucleophiles. Some chromone derivatives linked a variety of heterocyclic systems were prepared from the direct condensation of 3-formylchromones with heterocyclic compounds containing active methylene groups. A diverse number of fused heterocyclic systems were prepared from the reaction of 3-formylchromones with some bifunctional nucleophiles, these reactions mainly proceed via condensation with the aldehydic function followed by nucleophilic attack at C-2 position of the chromone moiety.

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Ali, T. E.-S.; Ibrahim, M. A.; El-Gohary, N. M.; El‐Kazak, A. M. 3-Formylchromones As Diverse Building Blocks in Heterocycles Synthesis. Eur. J. Chem. 2013, 4, 311-328.

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References

[1]. Reynolds, G. A.; Van Allan, J. A. J. Heterocycl. Chem. 1969, 6, 375-377.
http://dx.doi.org/10.1002/jhet.5570060316

[2]. Harnisch, H. Liebigs Ann. Chem. 1973, 765, 8-14.
http://dx.doi.org/10.1002/jlac.19727650103

[3]. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron Lett. 1973, 14, 1995-1998.
http://dx.doi.org/10.1016/S0040-4039(01)96102-7

[4]. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron 1974, 30, 3553-3561.
http://dx.doi.org/10.1016/S0040-4020(01)97034-6

[5]. Prakash, O.; Kumar, R.; Sharma, D.; Bhardwaj, V. J. Indian Chem. Soc. 2004, 81, 888-890.

[6]. Klutchko, S.; Cohen, M. P.; Shavel J. J.; Von Standtmann, M. J. Heterocycl. Chem. 1974, 11, 183-188.
http://dx.doi.org/10.1002/jhet.5570110214

[7]. Becket, G. J. P.; Ellis, G. P. Tetrahedron Lett. 1976, 17, 719-720.
http://dx.doi.org/10.1016/S0040-4039(00)74607-7

[8]. Ellis, G. P. J. Chem. Res (S). 1978, 47-48.

[9]. El-Shaaer, H. M. E.; Prejessy, A.; Zahradik, P.; Lacova, M.; Sustekova, Z. Monatch Chem. 1993, 124, 539-548.
http://dx.doi.org/10.1007/BF00819522

[10]. Eiden, F.; Haverland, H. Arch. Pharm. 1996, 5, 29-33.

[11]. Paul, S.; Gupta, R.; Gupta, M.; Loupy, A. Synthesis 2002, 75-78.
http://dx.doi.org/10.1055/s-2002-19308

[12]. Shim, Y. S.; Kim, K. C.; Chi, D. Y.; Lee, K. H.; Cho, H. Bioorg. Med. Chem. Lett. 2003, 13, 2561-2563.
http://dx.doi.org/10.1016/S0960-894X(03)00479-7

[13]. Shrestha, S.; Hwang, S. Y.; Lee, K. H.; Cho, H. Bull. Korean Chem. Soc. 2005, 26, 1138- 1140.
http://dx.doi.org/10.5012/bkcs.2005.26.7.1138

[14]. Nandgaonkar, R. G.; Ingle, V. N. Asian J. Chem. 2005, 17, 2016-2018.

[15]. Kamotra, P.; Gupta, A.K.; Gupta, R.Indian J. Chem. B 2007, 46, 866-868.

[16]. Hatzade, K. M.; Taile, V. S.; Gaidhane, P. K.; Umare, V. D.; Haldar, A. G. M.; Ingle, N. V. Indian J. Chem. B 2009, 48, 1548-1557.

[17]. Ibrahim, S. S.; Allimony, H. A.; Abdel-Halim, A. M.; Ibrahim, M. A. Arkivoc 2009, 14, 28-38.

[18]. Patil, L. R.; Ingle, V. S.; Bondge, S. P.; Mane, R. A. Indian J. Chem. 2001, 41B, 131-134.

[19]. Shankar, M. S. S.; Reddy, R. B.; Chandra, M. G. V. P.; Reddy, Y. D. J. Indian Chem. Soc. 1989, 66, 30-35.

[20]. Tuskaev, V. A.; Oganesyan, E. T.; Mutsueva, S. K. Pharm. Chem. J. 2002, 36, 309-312.
http://dx.doi.org/10.1023/A:1020828607049

[21]. Hatzade, K. M.; Taile, V. S.; Gaidhane, P. K.; Halder, A. G. M.; Ingle, V. N. Indian J. Chem. B 2008, 47, 1260-1270.

[22]. Abass, M.; Abdel-Megid, M.; Hassan, M. Synth. Commun. 2007, 37, 329-352.
http://dx.doi.org/10.1080/00397910601033930

[23]. Abass, M.; Hassan, A. Chem. Pap. 2003, 57, 267-277.

[24]. Abdel-Megid, M.; Gabr, Y.; Awas, M. A.; Abdel-Fattah, N. M. Chem. Heterocycl. Compds. 2009, 45, 1354-1364.
http://dx.doi.org/10.1007/s10593-010-0433-1

[25]. Siddiqui, Z.N.; Musthafa, T. N. M. Tetrahedron Lett. 2011, 52, 4008-4013.
http://dx.doi.org/10.1016/j.tetlet.2011.05.118

[26]. Mustafa, T. N. M.; Siddiqui, Z. N.; Husain, F. M.; Ahmad, I. Med. Chem. Res. 2010, 19, 1473-1481.

[27]. Siddiqui, Z. N.; Asad, M.; Praveen, S. Med. Chem. Res. 2008, 17, 318-325.
http://dx.doi.org/10.1007/s00044-007-9067-y

[28]. El-Shaaer, H. M. Eur. J. Chem. 2012, 3, 51-56.
http://dx.doi.org/10.5155/eurjchem.3.1.51-56.500

[29]. Melikyan, G.; Lacova, M.; Kralova, K.; El-Shaaer, H. M.; Henselova, M.; Avetisyan, A. A. Chem. Pap. 1993, 47, 388-392.

[30]. Lacova, M.; El-Shaaer, H. M.; Loss, D.; Matulova, M.; Chovancova, J.; Furdik, M. Molecules 1998, 3, 120-131.
http://dx.doi.org/10.3390/30300120

[31]. Caujoll, R.; Baziard-Mouysset, G.; Favort, J. D.; Payard, M.; Loiseau, P. R.; Amaroush, H.; Linas, M. D.; Seguela, J. P.; Loiseau, P. M.; Bories, C.; Gayral, P. Eur. J. Med. Chem. 1993, 28, 29-35.
http://dx.doi.org/10.1016/0223-5234(93)90076-Q

[32]. Gasparova, R.; Lacova, M.; El-Shaaer, H. M.; Odlerova, Z. II Farmaco 1997, 52, 251-352.

[33]. Achaiah, G.; Jayamma, Y.; Reddy, V. M. Indian J. Heteterocycl. Chem. 1991, 1, 139-143.

[34]. Karale, B. K.; Gill, C. H.; Ganages, K. N.; Bachute, M. T.; Shingare, M. S. Indian J. Heterocycl. Chem. 1999, 9, 153-154.

[35]. Karale, B. K.; Gill, C. H.; Ganage, K. N.; Bachute, M. T.; Shingare, M. S. Indian J. Heterocycl. Chem. 2003, 12, 267-270.

[36]. Carvaiho, S. A.; Desilva, E. F.; Desouza, M. N. N.; Lourence, M. C. S.; Reckova, R. R. F. Bioorg. Med. Chem. Lett. 2008, 18, 538-541.
http://dx.doi.org/10.1016/j.bmcl.2007.11.091
PMid:18068364

[37]. Joshi, R. S.; Mandhane, P. G.; Badadhe, P. V.; Gill, C. H. Ultrason. Sonochem. 2011, 18, 735-738.
http://dx.doi.org/10.1016/j.ultsonch.2010.11.001
PMid:21112230

[38]. Nohara, A.; Kuriki, H.; Saijo, T.; Ukawa, K.; Murata, T.; Kanno, M.; Sanno, Y. J. Med. Chem. 1975, 18, 34-37.
http://dx.doi.org/10.1021/jm00235a008

[39]. Karale, B. K.; Chavan, V. P.; Hangarge, R. V.; Mane, A. S. Indian J. Heterocycl. Chem. 2001, 11, 81-82.

[40]. Halnor, V. B.; Dalvi, N. R.; Joshi, N. S.; Gill, C. H.; Karale, B. K. Indian J. Chem. B 2006, 45, 288-291.

[41]. Lacova, M.; Stankovcova, H.; Bohac, A.; Kotzianova, B. Tetrahedron 2008, 64, 9646-9653.
http://dx.doi.org/10.1016/j.tet.2008.07.032

[42]. Lacova, M.; GaSparova, R.; Kois, P.; Bohac, A.; El-Shaaer, H. M. Tetrahedron 2010, 66, 1410-1419.

[43]. Kovacikova, L.; GaSparova, R.; Bohac, A.; Durana, M.; Lacova, M. Arkivoc 2010, 11, 188-203.

[44]. Shingare, M. S.; Karale, B. K.; Gill, C. H.; Ganage, K. N.; Bachute, M. T. Indian J. Heterocycl. Chem. 1999, 9, 153-154.

[45]. Kois, P.; El-Shaaer, H. M.; Lacova, M. 6thElectronic Conference on Synthetic Organic Chemistry, ECSOC-9, September 1-30, 2005.

[46]. Nohara, A.; Umetani, T.; Sanno, Y. Jap. Patent, 1975, 7, 552067; C. A., 1976, 84, 105400t.

[47]. Nohara, A.; Kuriki, H.; Saijo, T.; Sugihara, H.; Kanno, M.; Sanno, Y. J. Med. Chem. 1977, 20, 141-145.
http://dx.doi.org/10.1021/jm00211a030

[48]. Gill, C. H.; Karale, B. K.; Dalvi, N. R. Indian J. Chem. B 2005, 44, 1522-1525.

[49]. Diwakar, S. D.; Bhagwat, S. S.; Shingare, M. S.; Gill, C. H. Bioorg. Med. Chem. Lett. 2008, 18, 4678-4681.
http://dx.doi.org/10.1016/j.bmcl.2008.07.007
PMid:18650090

[50]. Luengo, J. I.; Elliott, J. D.; Xiang, J. N. PCT. Int. Appl. Wo. 97 04, 773; C. A., 1997, 126, 225307g.

[51]. Nadiu, M. S. R.; Nadiu, R. R. Indian J. Chem. B 1997, 36, 99-100.

[52]. Prousek, J.; Jurasek, A.; Kovac, J. Coll. Czech. Chem. Commun. 1980, 45, 1704-1706.

[53]. Jones W. D.; Albrecht, W. L. J. Org. Chem. 1976, 41, 706-707.
http://dx.doi.org/10.1021/jo00866a028

[54]. Bandyophadyaya, C.; Sur, K. R.; Patra, R. J. Chem. Res. (s). 1998, 12, 802-803.

[55]. Borrell, J. I.; Teixido, J.; Schuler, E.; Michelotti, E. L. Molecular Diversity 2000, 5, 163- 166.
http://dx.doi.org/10.1023/A:1016246405906

[56]. Hangarge, R. V.; Sonwane, S. A.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2001, 3, 310-312.
http://dx.doi.org/10.1039/b106871g

[57]. Chandra, K. G.; Samita, B.; Nanda, G.; Basudeb, A. J. Chem. Res(s). 1998, 178-179.

[58]. Saha, S. S.; Ghosh, T.; Tarun, G.; Bandyopadhyay, C. Synth. Commun. 2008, 38, 2429-2436.
http://dx.doi.org/10.1080/00397910802139049

[59]. Awas, M. A. A. Chem. Pap. 2006, 60, 338-347.
http://dx.doi.org/10.2478/s11696-006-0062-4

[60]. Nohara, A.; Ishiguro, T.; Sanno, Y. Tetrahedron Lett. 1974, 13, 1183-1186.
http://dx.doi.org/10.1016/S0040-4039(01)82440-0

[61]. Abdel-Rahman, A. H.; Hammouda, M. A. A.; El-Desoky, S. I. Heteroatom. Chem. 2005, 16, 20-27.
http://dx.doi.org/10.1002/hc.20048

[62]. Heber, D. Synthesis 1978, 691-692.
http://dx.doi.org/10.1055/s-1978-24860

[63]. Ghosh, C. K.; Khan, S. Synthesis 1981, 903-907.
http://dx.doi.org/10.1055/s-1981-29642

[64]. Ghosh, C. K. Heterocycles 2004, 63, 2875-2898.
http://dx.doi.org/10.3987/REV-04-586

[65]. Terzidis, M.; Tsoleridis, C. A.; Stephanidou-Stephanatou, J. Tetrahedron 2007, 63, 7828-7862.
http://dx.doi.org/10.1016/j.tet.2007.05.100

[66]. Von Harnish, H. Justus Lieb. Ann. Chem. 1972, 765, 25-33.

[67]. Copeland, R. A. B.; Day, A. R. J. Am. Chem. Soc. 1943, 65, 1072-1075.
http://dx.doi.org/10.1021/ja01246a019

[68]. Brzozowski, Z.; Saczewski, F. Eur. J. Med. Chem. Chem. 2002, 37, 709-720.
http://dx.doi.org/10.1016/S0223-5234(02)01379-X

[69]. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2 007, 3155-3162.

[70]. Sarma, G. V. S. R.; Reddy, V. M. Indian J. Heterocycl. Chem. 1993, 3, 111-116.

[71]. Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Houghton, P. G. Synthesis 1977, 133-134.
http://dx.doi.org/10.1055/s-1977-24298

[72]. Sabitha, G.; Reddy, M. M.; Archana, B.; Yadav, J. S. Synth. Commun. 1998, 28, 573-581.
http://dx.doi.org/10.1080/00397919808005928

[73]. Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M.; Shivanyuk, A. N.; Tolmachev, A. A. Tetrahedron 2008, 64, 5933-5943.
http://dx.doi.org/10.1016/j.tet.2008.04.041

[74]. Naskar, S.; Banerjee, M.; Hazra, A.; Mondal, S.; Maity, A.; Paira, R.; Sahu, K. B.; Saha, P.; Banerjee, S.; Mondal, N. B. Tetrahedron Lett. 2011, 52, 1527-1531.
http://dx.doi.org/10.1016/j.tetlet.2011.01.141

[75]. Polyakov, V. K.; Shevtsova, R. G.; Tsukerman, S. Ukr. Khim. Zh, 1981, 47, 85-87.

[76]. Haas, G.; Stanton, J. L.; Von Sprecher, A.; Wenk, P. J. Heterocycl. Chem. 1981, 18, 607- 612.
http://dx.doi.org/10.1002/jhet.5570180334

[77]. Singh, P.; Kaur, M.; Holzer, W. Eur. J. Med. Chem. 2010, 45, 4968-4082.
http://dx.doi.org/10.1016/j.ejmech.2010.08.004
PMid:20810192

[78]. Karale, B. K.; Chavan, V. P.; Mane, A. S.; Hangarge, R. V.; Gill, C. H.; Shingare, M. S. Synth. Commun. 2002, 32, 497-503.
http://dx.doi.org/10.1081/SCC-120002395

[79]. Siddiqui, Z. N.; Musthafa, T. N. M.; Praveen, S. Med. Chem. Res. 2013, 22, 127-133.
http://dx.doi.org/10.1007/s00044-012-0013-2

[80]. Khodairy, A. J. Chinese Chem. Soc. 2007, 54, 93-102.

[81]. Shelke, S. N.; Dalvi, N. R.; Kale, S. B.; More, M. S.; Gill, C. H.; Karale B. K. Indian J. Chem. B 2007, 46, 1174-1178.

[82]. Abbas, M.; Othman, E. S.; Hassan, A. Synth. Commun. 2007, 37, 607-621.
http://dx.doi.org/10.1080/00397910601055180

[83]. Lacova, M.; GaSparova, R.; Loos, D.; Liptay, T.; Pronayova, N. Molecules 2000, 5, 167- 178.
http://dx.doi.org/10.3390/50200167

[84]. Bozdag-Dundar, O.; Evranos, B.; Das-Evcimen, N.; Sarhkaya, M.; Ertan, R. Eur. J. Med. Chem. 2008, 43, 2412-2417.
http://dx.doi.org/10.1016/j.ejmech.2008.01.004
PMid:18313804

[85]. Verspohl, E. J.; Bozdağ-Dündar, O.; Kaup, R. M.; Bauer, K.; Ertan, R. Med. Chem. Res. 2009, 18, 665-670.
http://dx.doi.org/10.1007/s00044-008-9158-4

[86]. Ibrahim, M. A.; Abdel-megid, M.; El-Gohary, N. M. J. Braz. Chem. Soc. 2011, 21, 1130- 1139.
http://dx.doi.org/10.1590/S0103-50532011000600019

[87]. GaSparova, R.; Lacova, M. Coll. Czech. Commun. 1995, 60, 1178-1183.

[88]. Franz, C.; Heinisch, G.; Holzer, W.; Mereiter, K.; Strobe, B.; Zheng, C. Heterocycles 1995, 41, 2527-2551.
http://dx.doi.org/10.3987/COM-95-7203

[89]. Shutov, R. V.; Kukline, E. V.; Ivin, B. A. Russ. J. Gen. Chem. 2009, 79, 1049-1051.
http://dx.doi.org/10.1134/S107036320905034X

[90]. Eiden, F.; Haverland, H. Arch. Pharm. 1967, 300, 806-809.
http://dx.doi.org/10.1002/ardp.19673000911

[91]. Shelke, K. F.; Sapkal, K. S. B.; Niralwad, S.; Shingate, B. B.; Shingate, M. S. Cent. Eur. J. Chem. 2010, 8, 12-18.
http://dx.doi.org/10.2478/s11532-009-0111-2

[92]. Shindalkar, S. S.; Madje, B. R.; Shingare, M. S. Indian J. Chem. B 2006, 45, 2571-2573.

[93]. Prousek, J. Coll. Czech. Chem. Commun. 1991, 56, 1361.
http://dx.doi.org/10.1135/cccc19911361

[94]. Reddy, K. V.; Rao, A. V. S. Org. Prep. Proc. Int. 1997, 29, 355-357.
http://dx.doi.org/10.1080/00304949709355212

[95]. Sosnovskikh, V. Y.; Irgashev, R. A.; Levchenko, A. A. Tetrahedron 2008, 64, 6607-6614.
http://dx.doi.org/10.1016/j.tet.2008.05.032

[96]. Teimouri, M. B. Tetrahedron 2011, 67, 1837-1843.
http://dx.doi.org/10.1016/j.tet.2011.01.033

[97]. Bandyopadhyay, C.; Sur, K. R. Indian. J. Chem. B 2000, 39, 137-140.

[98]. Ibrahim, M. A.; Hassanin, H. M.; Gabr, Y. A.; Alnamer, Y. A. Eur. J. Chem. 2010, 3, 195-199.
http://dx.doi.org/10.5155/eurjchem.1.3.195-199.91

[99]. Hassanin, H. M.; Ibrahim, M. A.; Alnamer, Y. A. Turkish J. Chem. 2012, 36, 682-699.

[100]. Fitton, A. O.; Frost, J. R.; Suschitzky, H. Tetrahedron Lett. 1975, 16, 2099-2100.
http://dx.doi.org/10.1016/S0040-4039(00)75305-6

[101]. Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1982, 65, 26.
http://dx.doi.org/10.1002/hlca.19820650128

[102]. Achaiah, C.; Reddy, V. Indian J. Pharm. Sci. 1991, 53, 253-255.

[103]. Chen, H. M.; Cao, L. H. J. Chinese Chem. Soc. 2009, 56, 1028-1034.

[104]. Kapur, A.; Kumar, K.; Singh, L.; Singh, P.; Elango, M.; Subramanian, V.; Gupta, V.; Kanwal, P.; Ishar, M. P. S. Tetrahedron 2009, 65, 4593-4603.
http://dx.doi.org/10.1016/j.tet.2009.03.076

[105]. Khan, K. M.; Ambreen, N.; Hussain, S.; Perveen, S.; Choudhary, M. I. Bioorg. Med. Chem. 2009, 17, 2983-2988.
http://dx.doi.org/10.1016/j.bmc.2009.03.020
PMid:19329330

[106]. Khan, K. M.; Ambreen, N.; Mughal, U. R.; Jalil, S.; Perveen, S.; Choudhary, M. I. Eur. J. Med. Chem. 2010, 45, 4058-4064.
http://dx.doi.org/10.1016/j.ejmech.2010.05.065
PMid:20576329

[107]. Dziewulska-Kulaczkowska, A. J. Therm. Anal. Calorim. 2012, 109, 7-15.
http://dx.doi.org/10.1007/s10973-011-1387-y

[108]. El-Shaaer, H. M.; Abdel-Aziz, S. A. A.; Hanafy, F. I.; Ali, T. E.; El-Fayomy, A. Z. Eur. J. Chem. 2011, 2, 158-162.
http://dx.doi.org/10.5155/eurjchem.2.2.158-162.381

[109]. Fitton, A. O.; Haughyo, G.; Suschitzky, H. Synthesis 1979, 337-339.
http://dx.doi.org/10.1055/s-1979-28669

[110]. Lacova, M.; Stankovicova, H.; Odlerova, Z. II Farmaco 1995, 50, 885-888.

[111]. Fitton, A. O.; Frost, J. R.; Houghton, P. G.; Suschitzky, H. J. Chem. Soc., Perkin Trans. 1 1977, 1450-1452.

[112]. El-Shaaer, H. M.; Foltinova, P.; Lacova, M.; Chovancova, J.; Stankovicova, H. II Farmaco 1998, 53, 224-232.
http://dx.doi.org/10.1016/S0014-827X(98)00015-9

[113]. Stankovicova, H.; Lacova, M.; Gaplovsky, A.; Chovancova, J.; Pronayova, N. Tetrahedron 2001, 57, 3455-3464.
http://dx.doi.org/10.1016/S0040-4020(01)00219-8

[114]. Al-Rashida, M.; Ashraf, M.; Hussain, B.; Nagra, S. A.; Abbas, G. Bioorg. Med. Chem. 2011, 19, 3367-3371.
http://dx.doi.org/10.1016/j.bmc.2011.04.040
PMid:21555223

[115]. Dziewulska-Kulaczkowska, A.; Mazur, L. J. Mol. Struct. 2011, 985, 233-244.
http://dx.doi.org/10.1016/j.molstruc.2010.10.049

[116]. Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M.; Gavrilenko, K. S.; Shivanyuk, A. N.; Tolmachev, A. A. J. Org. Chem. 2008, 73, 6010-6013.
http://dx.doi.org/10.1021/jo800950y
PMid:18593188

[117]. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2007, 1861-1871.

[118]. Kalanithi, M.; Kodimunthiri, D.; Rajarajan, M.; Tharmaraj, P. Spectrochim. Acta A 2011, 82, 290-298.
http://dx.doi.org/10.1016/j.saa.2011.07.051
PMid:21824811

[119]. Clarke, P. D.; Fitton, A. O.; Kosmirak, M.; Suschitzky, H.; Suschitzky, J. L. J. Chem. Soc., Perkin Trans. 1 1985, 1747-1756.

[120]. Ghosh, C. K.; Ray, A.; Patra, A. J. Heterocycl. Chem. 2001, 38, 1459-1463.
http://dx.doi.org/10.1002/jhet.5570380632

[121]. Fitton, A. O.; Kosmırak, M.; Suschıtzky, H. Tetrahedron Lett. 1982, 23, 3953-3956.
http://dx.doi.org/10.1016/S0040-4039(00)87752-7

[122]. Nogueras, M.; Sanchez, A.; Cobo, J.; Low, J. N. J. Heterocycl. Chem. 2002, 49, 51-54.

[123]. Lacova, M.; Puchala, A.; Solčanyova, E.; Lac, J.; Kois, S.; Chovancova, J.; Rsala, D. Molecules 2005, 10, 809-821.
http://dx.doi.org/10.3390/10070809
PMid:18007351

[124]. Eynde, J. J. V.; Hecq, N.; Kataeva, O.; Kappe, C. O. Tetrahedron 2001, 57, 1785-1791.
http://dx.doi.org/10.1016/S0040-4020(00)01157-1

[125]. Quiroga, D.; Rengifo, A.; Insuasty, B.; Abonía, R.; Nogueras, M.; Sanchez, A. Tetrahedron Lett. 2002, 43, 9061-9063.
http://dx.doi.org/10.1016/S0040-4039(02)02316-X

[126]. Abonia, R.; Insusty, B.; Quiroga, J.; Kolshorn, H.; Meier, H. J. Heterocycl. Chem. 2001, 38, 671-674.
http://dx.doi.org/10.1002/jhet.5570380321

[127]. Kubicova, L.; Pour, M.; Lacova, M.; Kralova, K.; Chovancova, J.; Kaustova, J. 9thElectronic Conference on Synthetic Organic Chemistry, ECSOC-9, September 1-30, 2002.

[128]. Reddy, G. J.; Sabitha, M. G.; Rao, A. V. S. Synth. Commun. 1987, 17, 1851-1859.
http://dx.doi.org/10.1080/00397918708077331

[129]. Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M.; Shivanyuk, A. N.; Tolmachev, A. A. Heterocycles 2008, 75, 1765-1772.
http://dx.doi.org/10.3987/COM-08-11347

[130]. Ghosh, C. K.; Khan, S. Synthesis 1980, 9, 701-702.
http://dx.doi.org/10.1055/s-1980-29176

[131]. Reddy, G. J.; Rao, A. V. S. Curr. Sci. 1981, 50, 84-86.

[132]. Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1982, 65, 275-279.
http://dx.doi.org/10.1002/hlca.19820650128

[133]. Rihs, G.; Sigg, I.; Haas, G.; Winkler, T. Helv. Chim. Acta 1985, 68, 1933-1935.
http://dx.doi.org/10.1002/hlca.19850680717

[134]. Risitano, F.; Grassi, G.; Foti, F. J. Heterocycl. Chem. 2001, 38, 1083-1086.
http://dx.doi.org/10.1002/jhet.5570380511

[135]. Abdel-Rahman, A. H.; Khalil, A. M.; Keshk, E. M. Boll. Chim. Farm. 2001, 140, 387-396.
PMid:11822227

[136]. Grolik, J.; Zwolinski, K.; Eilmes, J.; Sieron, L. Tetrahedron 2011, 67, 2623-2632.
http://dx.doi.org/10.1016/j.tet.2011.02.010

[137]. Grolik, J.; Sieron, L.; Eilmes, J. Tetrahedron Lett. 2006, 47, 8209-8213.
http://dx.doi.org/10.1016/j.tetlet.2006.09.134

[138]. Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett. 2007, 48, 61-64.
http://dx.doi.org/10.1016/j.tetlet.2006.11.018

[139]. Maiti, S.; Panja, S. K.; Bandyopadhyay, C. Indian J. Chem. 2009, 48B, 1447-1452.

[140]. El-Desoky, E. I.; Al-Shihry, S. S. J. Heterocycl. Chem. 2008, 45, 1855-1864.
http://dx.doi.org/10.1002/jhet.5570450648

[141]. Das, B.; Kanth, B. S.; Reddy, K. R.; Kumar, A. S. J. Heterocycl. Chem. 2008, 45, 1499- 1502.
http://dx.doi.org/10.1002/jhet.5570450542

[142]. Ali, T. E.; Ibrahim, M. A. J. Braz. Chem. Soc. 2010, 21, 1007-1016.
http://dx.doi.org/10.1590/S0103-50532010000600010

[143]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z. Turk. J. Chem. 2008, 32, 365-374.

[144]. Ghosh, C. K.; Khan, S. Synthesis 1981, 719-720.
http://dx.doi.org/10.1055/s-1981-29574

[145]. Shelke, S. N.; Dalvi, N. R.; Shingare, M. S.; Gill, C. H.; Karale, B. K. Indian J. Heterocycl. Chem. 2006, 15, 403-404.

[146]. Sharad, N. S.; Sonawane, M. P.; Karale, B. K.; Gill, C. H. Nature Precedings 2009, 1, 2855-2862.

[147]. Pospisil, J.; Potacek, M. Heterocycles 2004, 63, 1165-1173.
http://dx.doi.org/10.3987/COM-03-9997

[148]. Gabbutt, C. D.; Hargrove, T. F. L.; Heron, B. M.; Jones, D.; Poyner, C.; Yildiz, E.; Horton, P. N.; Hursthouse, M. B. Tetrahedron 2006, 62, 10945-10953.
http://dx.doi.org/10.1016/j.tet.2006.08.090

[149]. Ghosh, C. K.; Mukhopdyaya, K. K. J. Indian Chem. Soc. 1978, 55, 52-55.

[150]. Ghosh, C. K.; Mukhopdyaya, K. K. J. Indian Chem. Soc. 1978, 55, 386-388.

[151]. Reddy, G. J.; Sbitha, G.; Rao, A. V. S. Indian J. Chem. B 1984, 23, 99-103.

[152]. Nawrot-Modranka, J.; Nawrot, E.; Graczyk, J. Eur. J. Med. Chem. 2006, 41, 1301-1309.
http://dx.doi.org/10.1016/j.ejmech.2006.06.004
PMid:16904795

[153]. Lazrenkow, A.; Nawrot-Modranka, J.; Brzeziska, E.; Krojewska, U. R.; Ozalski, M. Med. Chem. Res. 2012, 21, 1861-1868.
http://dx.doi.org/10.1007/s00044-011-9703-4

[154]. Ghosh, C. K.; Sinharoy, D. K.; Mukhopadhyaya, K. K. J. Chem. Soc., Perkin Trans. 1 1979, 1981-1985.

[155]. Bosinski, W.; Jerzmanowska, Z. Pol. J. Chem. 1983, 57, 471-474.

[156]. Petersen, U.; Heitzer, H. Liebigs Ann. Chem. 1976, 1663-1666.

[157]. Sosnovskikh, V. Y.; Moshkin, V. S.; Kodess, M. I.; Tetrahedron Lett. 2008, 49, 6856- 6859.
http://dx.doi.org/10.1016/j.tetlet.2008.09.091

[158]. Sosnovskikh, V. Y.; Moshkin, V. S.; Kodess, M. I. Mendeleev Commun. 2010, 20, 209- 211.
http://dx.doi.org/10.1016/j.mencom.2010.06.009

[159]. Maiti, S.; Panja, S. K.; Bandyopodhyay, C. Tetrahedron Lett. 2009, 50, 3966-3969.
http://dx.doi.org/10.1016/j.tetlet.2009.04.087

[160]. Ishar, M. P. S.; Kumar, K.; Singh, R. Tetrahedron Lett. 1998, 39, 6547-6550.
http://dx.doi.org/10.1016/S0040-4039(98)01362-8

[161]. Lowe, W. Synthesis 1976, 274-276.
http://dx.doi.org/10.1055/s-1976-24020

[162]. Ghosh, C. K.; Khan, S. C. Indian J. Chem. B 1979, 18, 128-130.

[163]. Pene, C.; Hubert-Habart, M. J. Heterocycl. Chem. 1980, 17, 61-64.
http://dx.doi.org/10.1002/jhet.5570170223

[164]. Crowther, A. F.; Curd, F. H. S.; Richardson, D. N.; Rose, F. L. J. Chem. Soc. 1984, 1636.

[165]. Borrell, J. I.; Teixido, J.; Schuler, E.; Michelotti, E. Tetrahedron Lett. 2001, 42, 5331- 5334.
http://dx.doi.org/10.1016/S0040-4039(01)00999-6

[166]. Bruno, O.; Brullo, C.; Ranis, A.; Schenone, S.; Bondavalli, F.; Barocelli, E.; Chivarini, M.; Ballabeni, V.; Impicciatore, M.; Tognolini, M. Bioorg. Med. Chem. Lett. 2011, 11, 1397-1400.
http://dx.doi.org/10.1016/S0960-894X(01)00221-9

[167]. Tsao, L.; Van, V.; Sun, G.; Lyu, Y. Russ. J. Gen. Chem. 2001, 71, 767-769.
http://dx.doi.org/10.1023/A:1012369621168

[168]. Cao, L. H.; Huang, Y. L. Y. T.; Sun, G. Z. Yingyong Huaxue 2001, 18, 312-313.

[169]. Foltinova, P.; Lacova, M.; Loss, D. II Farmaco2000, 55, 21-26.
http://dx.doi.org/10.1016/S0014-827X(99)00114-7

[170]. Cao, L.; Wang, W. Chem. Heterocycl. Compd. 2003, 39, 1072-1075.
http://dx.doi.org/10.1023/B:COHC.0000003526.98678.6e

[171]. Wang, B. D.; Yang, Z. Y.; Zhang, D. W.; Wang, Y. Spectrochim. Acta A 2006, 63, 213-219.
http://dx.doi.org/10.1016/j.saa.2005.05.007
PMid:15951232

[172]. Tsao, L.; Chzhan, L.; Lyu, T. Chem. Nat. Compd. 2001, 37, 311-314
http://dx.doi.org/10.1023/A:1013754030975

[173]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z. Phosphorous, Sulfur and Silicon Rel. Elem. 2008, 183, 2139-2160.
http://dx.doi.org/10.1080/10426500701851291

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