An Efficient and Rapid Synthesis of 2-amino-4-arylthiazoles Employing Microwave Irradiation in Water

Abstract

A facile, high yielding green chemical synthetic protocol adaptable to the parallel synthesis of a library of potentially bioactive 2-amino-4-arylthiazoles is reported herein. The methodology involves the condensation of various aracyl bromides with N-arylthioureas under MWI using water as solvent, to yield pure products (81%-97%) in very short reaction times (1-20 min).

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K. Jain, J. Bariwal, M. Kathiravan, V. Raskar, G. Wankhede, N. Londhe and S. Dighe, "An Efficient and Rapid Synthesis of 2-amino-4-arylthiazoles Employing Microwave Irradiation in Water," Green and Sustainable Chemistry, Vol. 1 No. 2, 2011, pp. 35-38. doi: 10.4236/gsc.2011.12007.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] M. Schnürch, B. Waldner, K. Hilber and M. D. Mihovilovic, “Synthesis of 5-arylated N-Arylthiazole-2-amines as Potential Skeletal Muscle Cell Differentiation Promoters,” Bioorganic & Medicinal Chemistry Letters, Vol 21, No. 7, 2011, pp 2149-2154. doi:10.1016/j.bmcl.2011.01.123
[2] N. Vukovic, S. Sukdolak, S. Solujic and T. Milosevic, “Synthesis and Antimicrobial Evaluation of Some Novel 2-Aminothiazole Derivatives of 4-hydroxy-Chromene-2- one,” Arch Pharm (Weinheim), Vol. 341, No. 8, 2008, pp 491-496. doi:10.1002/ardp.200700215
[3] De Logu A, M. Saddi, M. C. Cardia, R. Borgna, C. Sanna, B. Saddi and E. Maccioni, “In Vitro Activity of 2-Cyclo- Hexylidenhydrazo-4-phenyl-thiazole Compared with those of Amphotericin B and Fluconazole against Clinical Isolates of Candida Spp. and Fluconazole-Resistant Candida Albicans,” Journal of Antimicrobial Che- motherapy, Vol. 55, No. 5, 2005, pp. 692-698. doi:10.1093/jac/dki084
[4] Q. Al-Balas, N. G. Anthony, B. Al-Jaidi, A. Alnimr, G. Abbott, A. K. Brown, R. C. Taylor, G. S. Besra, T. D. McHugh, S. H. Gillespie, B. F. Johnston and S. P. Mackay, G. D. Coxon, “Identification of 2-ami-no- thiazole-4-car-boxylate Derivatives Active against Mycobacterium Tuberculosis H37rv And The Beta-Ketoacyl- Acp Synthase Mtfabh,” PLoS One, Vol. 4, No. 5, 2009, pp. 5617-5621. doi:10.1371/journal.pone.0005617
[5] T. K. Venkatachalam, E. A. Sudbeck, C. Mao and F. M. Uckun, “Anti-HIV Activity of Aromatic and Heterocyclic Thiazolyl Thiourea Compounds,” Bioorganic & Medicinal Chemistry Letters, Vol. 11, No. 4, 2001, pp 523-528. doi:10.1016/S0960-894X(01)00011-7
[6] M. C. Wilkes, P. B. Lavrik and J. Greenplate, “Synthesis of N-Benzoyl-N-Alkyl-2-aminothiazoles: Heliothis Virescens Proinsecticides” Journal of Agricultural Food Chemistry, Vol. 39, No. 9, 1991, pp. 1652-1657. doi:10.1021/jf00009a023
[7] B. S. Holla, K. V. Malini, B. S. Rao, B. K. Sarojini and N. Suchetha Kumari, “Synthesis of Some New 2,4-disub- Stituted Thiazoles as Possible Antibacterial and Anti-In- Flammatory Agents,” European Journal of Medicinal Chemistry, Vol 38, No. 3, 2003, pp. 313-318. doi:10.1016/S0223-5234(02)01447-2
[8] D. C. Warhurst, I. S. Agadu, D. Nolder, and J. F. Rossignol, “In Vitro Activity of Nitazoxanide and Related Compounds against Isolates of Giardia Intestinalis, Entamoeba Histolytica and Trichomonas Vaginalis,” Journal of Antimicrobial Chemotherapy, Vol. 49, No. 1, 2002, pp. 103-111.
[9] D. V. Jawale, D. L. Lingampalle, U. R. Pratap and R. A. Mane, “One-Pot Synthesis of 2-aminothiazoles in PEG- 400,” Chinese Chemical Letters, Vol 21, No. 4, 2010, pp. 412-416. doi:10.1016/j.cclet.2009.11.035
[10] P. C. Kearney, M. Fernandez, J. A. Flygare, “Solid-Phase Synthesis of 2-aminothiazoles”, Journal of Organic Chemistry, Vol. 63, No. 1, 1998, pp. 196-200. doi:10.1021/jo971542a
[11] N. Bailey, A. W. Dean, D. B. Judd, D. Middlemiss, R. Storer and S. P. Watson ,“A Convenient Procedure for the Solution Phase Preparation of 2-aminothiazole Combinatorial Libraries,” Bioorganic & Medicinal Chemistry Letters, Vol. 6, No. 12, 1996, pp. 1409-1414. doi:10.1016/0960-894X(96)00241-7
[12] B. Das, V. S. Reddy and R. Ramu, “A Rapid and High-Yielding Synthesis of Thiazoles and Aminothia- zoles Using Ammonium-12-molybdophosphate,” Journal of Molecular Catalysis A: Chemical, Volume 252, No. 1-2, 2006, pp. 235-237. doi:10.1016/j.molcata.2006.02.065
[13] N. M. Reddy, M. Somi, Sridhar, R. Nageswar, Y. V. D. Rao and K. Rama, “Aqueous Phase Synthesis of Thiazoles and Aminothiazoles in the Presence of b-cyc- lo-dextrin,” Tetrahedron Letters, Vol 46, No. 35, 2005, pp. 5953-5961. doi:10.1016/j.tetlet.2005.06.130
[14] M. Kidwai, D. Bhatnagar, P. Mothsra, A. K. Singh, S. Dey, “Molecular Iodine as a Versatile Reagent for Hantzsch Synthesis of 2-Aminothiazole Derivatives,” Journal of Sulfur Chemistry, Vol. 30, No. 1, 2009, pp. 29-36. doi:10.1080/17415990802422365
[15] H. N. Karade, M. Sathe and M. P. Kaushik, “Synthesis of 4-aryl Substituted 3, 4-dihydropyrimidinones Using Silica-chloride Under Solvent Free Conditions,” Molecules 2007, Vol 12, No. 7, pp 1341-1351. doi:10.3390/12071341
[16] I. Yavari, S. Z. Sayyed-Alangi, R. Hajinasiri and H. Sajjadi-Ghotbabadi, “A One-Pot Synthesis of Functionalized Ethyl 1,3-Thiazole-5-Carboxylates From Thioamides or Thioureas and 2-chloro-1,3-dicarbonyl Compounds in an Ionic Liquid,” Monatshefte für Chemie, Vol 140, No. 2, pp. 209-211. doi:10.1007/s00706-008-0065-7
[17] S. I. Zav’yalov, O. V. Dorofeeva, E. E. Rumyantseva, L. B. Kulikova, G. I. Ezhova, N. E. Kravchenko and A. G. Zavozin, “Synthesis of 2-aminothiazole Derivatives,” Pharmaceutical Chemistry Journal, Vol 35, No. 2, pp. 96-98. doi:10.1023/A:1010477022450
[18] C.-J. Li, “Water as Solvent for Organic and Material Synthesis, Green Chemical Syntheses and Processes,” ACS Symposium Series, Chapter 6, Vol. 767, pp. 62-73.
[19] J. B. Bariwal, J. C. Trivedi and Erik V. Van der Eycken, “Microwave Irradiation and Multi-component Reactions,” Topics in Heterocyclic Chemistry, Vol. 25, 2010, pp. 169-230.
[20] M. S. Phoujdar, M. K. Kathiravan, J. B. Bariwal, A. K. Shah and K. S. Jain, “Microwave-Based Synthesis of Novel Thienopyrimidine Bioisosteres of Gefitinib,” Tetrahedron Letters, Vol. 49, No. 7, 2008, pp 1269-1273. doi:10.1016/j.tetlet.2007.11.135
[21] “Vogel’s Textbook of Practical Organic Chemistry,” edited by, B. S. Furniss, A. J. Hannaford, P. W. G. Smith. and A. R. Tatchell, 5th Edition, ELBS Publication, pp.. 1050-1051.
[22] “Dictionary of Organic Compounds,” Chapman & Hall Electronic Publishing Division, UK, Vol. 5, 1996, p. 4823, 5348.

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