Bulletin of the Korean Chemical Society

  • 제33권6호
  • /
  • Pages.2012-2016
  • /
  • 2012
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

An Efficient Synthesis of New Pyrazolines and Isoxazolines Bearing Thiazolyl and Etheral Pharmacophores

  • Bhosle, Manisha R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Mali, Jyotirling R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Pratap, Umesh R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Mane, Ramrao A. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
  • 투고 : 2012.02.13
  • 심사 : 2012.03.24
  • 발행 : 2012.06.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

A convenient synthetic route has been developed to synthesize 5-(4-((2-phenylthiazol-4-yl) methoxy)phenyl)-3-(4-sustituted phenyl)pyrazolines (5a-f) and 5-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-3-(4-substituted phenyl)isoxazolines (6a-f) starting from 2-phenyl-4-chloromethylthiazole (1). The chloromethylthiazole (1) was first condensed with 4-hydroxy benzaldehyde (2) for obtaining 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3). Claisen-Smidth condensation of 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3) and acetophenones has been carried in alkaline alcohol and obtained 3-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-1-(4-substituted phenyl)prop-2-en-1-ones (4a-f). The cyclocondensation of 2-propen-1-ones has been first time carried separately with hydrazine hydrate and hydroxylamine hydrochloride in aqueous micellar tetradecyltrimethylammonium bromide (TTAB) medium for getting the titled heterocycles with good to excellent yields.

키워드

참고문헌

  1. Vita-Finzi, P. The Chemistry of Heterocyclic Compounds; Wiley and Sons: New York, 1991; 4, part-1, p 417.
  2. Nauduri, D.; Reddy, G. B. Chem. Pharma. Bull. 1998, 46, 1254. https://doi.org/10.1248/cpb.46.1254
  3. Hoffer, M., US Patent, 2721200, 1995.
  4. Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Zaprutko, L.; Lesyk, R. Eur. J. Med. Chem. 2009, 44, 1396. https://doi.org/10.1016/j.ejmech.2008.09.032
  5. Chiminchi, S.; Boccalini, M.; Hassan, M. M.; Viola, G.; Dall, A. F.; Curini, M. Tetrahedron 2006, 62, 90. https://doi.org/10.1016/j.tet.2005.09.135
  6. Korgaokar, S. S.; Patil, P. H.; Shah, M. J.; Parekh, H. H. Indian J. Pharm. Sci. 1996, 58, 222-225.
  7. Abid, M.; Bhat, A. R.; Athar, F.; Azam, A. Eur. J. Med. Chem. 2009, 44, 417. https://doi.org/10.1016/j.ejmech.2007.10.032
  8. Nugent, R. A.; Murphy, M.; Schlachter, S. T.; Dunn, C. J.; Smith, J. R.; Staite, N. D.; Galinet, A. L.; Asar, D. G.; Richard, K. A. J. Med. Chem. 1993, 36, 134. https://doi.org/10.1021/jm00053a017
  9. Manna, F.; Chimenti, F.; Balasco, A.; Cenicola, M. L.; Amico, M.; Parrilo, C.; Rossi, F.; Marmo, E. Eur. J. Med. Chem. 1992, 27, 633. https://doi.org/10.1016/0223-5234(92)90142-N
  10. Taylor, J.; Chandler, R.; Stauffer, J.; Harold, F., US Patent 4871737, 1989.
  11. Uno, H.; Kurokawa, M.; Masuda, Y.; Nishimura, H. J. Med. Chem. 1979, 22, 180. https://doi.org/10.1021/jm00188a011
  12. Taylor, E. S.; Patel, H. H. Tetrahedron 1992, 48, 8089. https://doi.org/10.1016/S0040-4020(01)80479-8
  13. Palaska, E.; Aytemir, M.; Uzbay, I. T.; Erol, D. Eur. J. Med. Chem. 2001, 36, 539. https://doi.org/10.1016/S0223-5234(01)01243-0
  14. Soliman, R.; Suzan, A. S.; Darwish, O. J. Med. Chem. 1983, 26(11), 1659. https://doi.org/10.1021/jm00365a023
  15. Hong, W. L.; Joong, B. A.; Sung, K. K.; Soon, K. A.; Deok, C. H. Org. Proc. Res. & Dev. 2007, 11, 190. https://doi.org/10.1021/op060087u
  16. Momura, M.; Kinoshita, S.; Satoh, H.; Maeda, T.; Murakami, K.; Tsunodam, M.; Miyachi, H.; Awano, K. Bioorg. Med. Chem. Lett. 1999, 9, 533. https://doi.org/10.1016/S0960-894X(99)00039-6
  17. Lewis, J. R. Nat. Prod. Rep. 1999, 16, 389. https://doi.org/10.1039/a802500b
  18. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719. https://doi.org/10.1021/ja01547a064
  19. Youssef, M. S.; Ahmed, R. A.; Abbady, M. S.; Abdel-Mohsen, S. A. Monatsh Chem. 2008, 139, 553. https://doi.org/10.1007/s00706-007-0817-9
  20. Clemence, F.; Marter, O. L.; Delevalle, F., Benzoni, J.; Jouanen, A.; Jouquey, S.; Deraedt, M. R. J. Med. Chem. 1988, 31, 1453. https://doi.org/10.1021/jm00402a034
  21. Tsuji, K., Ishikawa, H. Bioorg. Med. Chem. Lett. 1994, 4, 1601. https://doi.org/10.1016/S0960-894X(01)80574-6
  22. Li, J. T.; Zhang, X. H.; Lin, Z. P. Beilst. J. Org. Chem. 2007, 3, 13. https://doi.org/10.1186/1860-5397-3-13
  23. Molteni, V.; Hamilton, M. M.; Mao, L.; Crane, C. M.; Termin, A. P.; Wilson, D. M. Synthesis 2002, 12, 1669.
  24. Rajora, J.; Yadav, J.; Kumar, R.; Srivastava, Y. K. Indian J. Chem. 2010, 49, 989. https://doi.org/10.1021/ie900675d
  25. Kidwai, M.; Kukreja, S.; Thakur, R. Lett. Org. Chem. 2006, 3, 135. https://doi.org/10.2174/157017806775224170
  26. H3PW12Fazaeli, R.; Aliyan, H.; Bordbar, M.; Mohammadi, E. The Open Catly. J. 2010, 3, 79. https://doi.org/10.2174/1876214X01003010079
  27. Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Chem. Educ. 2004, 81, 874. https://doi.org/10.1021/ed081p874
  28. Anastas, P. T.; Warner, J. C. Green Chem. Theory and Practice; Oxford University Press: New York, 1998.
  29. Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. Mol. Diversity 2009, 13, 385. https://doi.org/10.1007/s11030-009-9122-3
  30. Grieco, P. A. Org. Synthes. In Water, Blackie Academic & Professional; London, 1998.
  31. Li, C. J.; Chang, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
  32. Matlack, A. S. Introduction to Green Chem.; Marcel Dekker, Inc.: New York, 2001.
  33. Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563. https://doi.org/10.1021/cr0509410
  34. Grieco, P. A. Organic Synthesis in Water; Blackie: London, 1998.
  35. Breslow, R. Acc. Chem. Res. 2004, 37, 471. https://doi.org/10.1021/ar040001m
  36. Azizi, N.; Aryanasab, F.; Torkiyan, L.; Ziyaei, A.; Saidi, M. R. J. Org. Chem. 2006, 71, 3634. https://doi.org/10.1021/jo060048g
  37. Tiwari, S.; Kumar, A. Angew. Chem. 2006, 118, 4942. Angew. Chem. Int. Ed. 2006, 45, 4824. https://doi.org/10.1002/anie.200600426
  38. Jung, Y.; Marcus, R. A. J. Am. Chem. Soc. 2007, 129, 5492. https://doi.org/10.1021/ja068120f
  39. Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systeams; Academic Press: London, 1975.
  40. Manabe, K.; Sun, X. M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 10101. https://doi.org/10.1021/ja016338q
  41. Shinde, P. V.; Kategaonkar, A. H.; Shingate, B. B.; Shingare, M. S. Beilst. J. Org. Chem. 2011, 7, 53. https://doi.org/10.3762/bjoc.7.9
  42. Shiri, M.; Zolfigol, M. A. Tetrahedron 2009, 65, 587. https://doi.org/10.1016/j.tet.2008.09.085
  43. Dandia, A.; Singh, R.; Bhaskaran, S.; Sarriant, S. D. Green Chem. 2011, DOI: 10.1039/c0gc00863.
  44. Jawale, D. V.; Pratap, U. R.; Rahuja, N.; Srivastava, A. K.; Mane, R. A. Bioorg. Med. Chem. Lett. 2012, 22, 436-439. https://doi.org/10.1016/j.bmcl.2011.10.110
  45. Pratap, U. R.; Jawale, D. V.; Waghmare, R. A.; Lingampalle, D. L.; Mane, R. A. New J. Chem. 2011, 35, 49. https://doi.org/10.1039/c0nj00691b
  46. Mali, J. R.; Bhosle, M. R.; Mahalle, S. R.; Mane, R. A. Bull. Korean Chem. Soc. 2010, 31, 1859. https://doi.org/10.5012/bkcs.2010.31.7.1859
  47. Bazargan, L.; Shafiee, A.; Amini, M.; Defouli, E. B.; Azizi, E.; Ghaffari, S. M. Phosph, Sulf. & Silicon 2009, 184, 602. https://doi.org/10.1080/10426500802239529
  48. Mahmoodi, M.; Aliabadi, A.; Emami, S.; Safavi, M.; Rajabalian, S.; Mohagheghi, M. A.; Khoshzaban, A.; Kermani, A. S.; Lamei, N.; Shafiee, A.; Foroumadi, A. Arch. Pharm. Chem. Life. Sci. 2010, 343, 411. https://doi.org/10.1002/ardp.200900198
  49. Wang, L. M.; Jiao, N.; Qiu, J.; Yu, J. J.; Liu, J. Q.; Guo, F. L.; Liu, Y. Tetrahedron 2010, 1, 339.
  50. Watanabe, Y.; Sawada, K.; Hayashi, M. Green Chem. 2010, 12, 384. https://doi.org/10.1039/b918349c
  51. Firouzabadi, H.; Iranpoor, N.; Garzan, A. Adv. Synth. Catal. 2005, 347, 1925. https://doi.org/10.1002/adsc.200505222

피인용 문헌

  1. )-3-Aryl-1-(3-alkyl-2-pyrazinyl)-2-propenone Synthesis in Water at Room Temperature vol.1, pp.8, 2013, https://doi.org/10.1021/sc400102e
  2. Tromethamine organocatalyzed efficient tandem-multicomponent synthesis of new thiazolyl-4-thiazolidinones in aqueous medium vol.49, pp.10, 2012, https://doi.org/10.1080/00397911.2019.1597124
  3. Organocatalyzed Domino Synthesis of New Thiazole‐Based Decahydroacridine‐1,8‐diones and Dihydropyrido[2,3‐d : 6,5‐d′]‐ dipyrimidines in Water as Antimicrobial vol.17, pp.2, 2012, https://doi.org/10.1002/cbdv.201900577