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Highly efficient microwave-assisted one-pot synthesis of 4-aryl-2-aminothiazoles in aqueous medium

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Abstract

The thiazole ring system is one of the most important heterocycles in nature, as it represents an important structural motif of many biological compounds, including vitamin B1 (Thiamin), carboxylase and penicillin. There is, therefore, an urgent need to design rapid, efficient and environmentally benign protocols for the synthesis of thiazoles. Herein, we have developed a one-pot protocol for the synthesis of 4-aryl-2-aminothiazoles from the reaction of aromatic ketones, NBS (N-Bromosuccinimide) and thioureas under microwave irradiation at 80–85 °C in PEG (polyethylene glycol)-400 and water as a green reaction medium. The products were obtained in 84–89% yields in 28–32 min. The method has several advantages such as use of green solvent, easy work-up, excellent yield and avoiding use of lachrymatric α-haloketones.

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References

  • Azizi N, Dezfooli S (2016) Catalyst-free synthesis of imidazo[1,2-a]pyridines via Groebke multicomponent reaction. Environ Chem Lett 14:201–206. doi:10.1007/s10311-015-0541-3

    Article  CAS  Google Scholar 

  • Bailey N, Dean AW, Judd DB, Middlemiss D, Storer R, Stephen PW (1996) A convenient procedure for the solution phase preparation of 2-aminothiazole combinatorial libraries. Bioorg Med Chem Lett 6:1409–1414. doi:10.1016/0960-894X(96)00241-7

    Article  CAS  Google Scholar 

  • Barbier-Baudry D, Brachais L, Cretu A, Gattin R, Loupy A, Stuerga D (2016) Synthesis of polycaprolactone by microwave irradiation—an interesting route to synthesize this polymer via green chemistry. Environ Chem Lett 1:19–23. doi:10.1007/s10311-002-0005-4

    Article  Google Scholar 

  • Chandrasekhar S, Narsihmulu C, Chandrasekhar G, Shyamsunder T (2004) Pd/CaCO3 in liquid poly (ethylene glycol) (PEG): easy and efficient recycle system for partial reduction of alkynes to cis-olefins under hydrogen atmosphere. Tetrahedron Lett 45:2421–2423. doi:10.1016/j.tetlet.2004.01.097

    Article  CAS  Google Scholar 

  • Clemence F, Marter OL, Delevalle F, Benzoni J, Joua-nen A, Jouquey S, Mouren M, Deraedt R (1988) 4-Hydroxy-3-quinolinecarboxamides with antiarthritic and analgesic activities. J Med Chem 31:1453–1462. doi:10.1021/jm00402a034

    Article  CAS  Google Scholar 

  • Das B, Saidi Reddy V, Ramu R (2006) A rapid and high-yielding synthesis of thiazoles and aminothiazoles using ammonium-12-molybdophosphate. J Mol Catal A: Chem 252:235–237. doi:10.1016/j.molcata.2006.02.065

    Article  CAS  Google Scholar 

  • Ei-Subbagh HI, AI-Obaid AM (1996) 2,4-Disubstituted thiazoles II. A novel class of antitumor agents, synthesis and biological evaluation. Eur J Med Chem 31:1017–1021. doi:10.1016/S0223-5234(97)86181-8

    Article  Google Scholar 

  • Fink BA, Mortensen DS, Stauffer SR, Aron ZD, Katzenel-lenbogen JA (1999) Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens. Chem Biol 6:205–219. doi:10.1016/S1074-5521(99)80037-4

    Article  CAS  Google Scholar 

  • Giltaire S, Herphelin F, Frankart A, Herin M, Stoppie P, Poumay Y (2009) The CYP26 inhibitor R115866 potentiates the effects of all-trans retinoic acid on cultured human epidermal keratinocytes. Br J Dermatol 160:505–513. doi:10.1111/j.1365-2133.2008.08960.x

    Article  CAS  Google Scholar 

  • Gupta S, Khanna G, Khurana JM (2016) A facile eco-friendly approach for the one-pot synthesis of 3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-diones using glycerol as a green media. Environ Chem Lett 14:559–564. doi:10.1007/s10311-016-0570-6

    Article  CAS  Google Scholar 

  • Hargrave KD, Hess FK, Oliver JT (1983) N-(4-substituted-thiazolyl)oxamicacid derivatives, a new series of potent, orally active anti-allergies agents. J Med Chem 26:1158–1163. doi:10.1021/jm00362a014

    Article  CAS  Google Scholar 

  • Jaen JC, Wise LD, Caprathe BW, Tecle H, Bergmeier S, Humblet CC, Heffner TG, Meltzner LT, Pugsley TA (1990) 4-(1,2,5,6-Tetrahydro-l-alkyl-3-pyridinyl)-2-thiazolamines: a novel class of compounds with central dopamine dgonist droperties. J Med Chem 33:311–317. doi:10.1021/jm00163a051

    Article  CAS  Google Scholar 

  • Kazzouli SE, Raboin SB, Mouadbib A, Guillau-met G (2002) Solid support synthesis of 2,4-disubstituted thiazoles and aminothiazoles. Tetrahedron Lett 43:3193–3196. doi:10.1016/S0040-4039(02)00471-9

    Article  Google Scholar 

  • Kim KS, Kimball SD, Misra RN, Rawlins DB et al (2002) Discovery of aminothiazole inhibitors of cyclin-dependent kinase 2: synthesis, X-ray crystallographic analysis and biological activities. J Med Chem 45:3905–3927. doi:10.1021/jm0201520

    Article  CAS  Google Scholar 

  • Kumar Y, Green R, Borysko KZ, Wise DS, Wotring LL, Townsend LB (1993) Synthesis of 2,4-disubstituted thiazoles and selenazoles as potential antitumor and antifilarial agents. 1. Methyl 4-(isothiocyanatomethyl)thiazole-2-carbamates, -selenazole-2-carbamates, and related derivatives. J Med Chem 36:3843–3848. doi:10.1021/jm00076a012

    Article  CAS  Google Scholar 

  • Kumavat PP, Jangale A, Patil DR, Dalal KS, Meshram JS, Dalal DS (2013) Green synthesis of symmetrical N,N′-disubstituted thiourea derivatives in water using solar energy. Environ Chem Lett 11:177–182. doi:10.1007/s10311-012-0394-y

    Article  CAS  Google Scholar 

  • Lednicer D, Mitscher LA, Georg GI (1990) Organic chemistry of drug synthesis, vol 4. Wiley, New York, pp 95–97

    Google Scholar 

  • Lewis JR (1999) Miscellaneous alkaloids: Amaryllidaceae, Sceletium, muscarine, imidazole, oxazole, peptide and other miscellaneous alkaloids. Nat Prod Rep 16:389–416. doi:10.1039/A802500B

    Article  CAS  Google Scholar 

  • Mirjafari A (2014) Direct synthesis of 2,4,5-trisubstituted imidazoles from alcohols and α-hydroxyketones by microwave. Environ Chem Lett 12:177–183. doi:10.1007/s10311-013-0423-5

    Article  CAS  Google Scholar 

  • Miwatashi S, Arikawa Y, Kotani E, Miyamoto M, Naruo KI, Kimura H, Tanaka T, Asahi S, Ohkawa S (2005) Novel inhibitor of p38 MAP kinase as an anti-TNF-α drug: discovery of N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridyl]benzamide (TAK-715) as a potent and orally active anti-rheumatoid arthritis agent. J Med Chem 48:5966–5979. doi:10.1021/jm050165o

    Article  CAS  Google Scholar 

  • Narender M, Somi Reddy M, Sridhar R, Nageswar YVD, Rama Rao K (2005) Aqueous phase synthesis of thiazoles and aminothiazoles in the presence of β-cyclodextrin. Tetrahedron Lett 46:5953–5955. doi:10.1016/j.tetlet.2005.06.130

    Article  CAS  Google Scholar 

  • Pereira R, Gaudon C, Iglesias B, Germain P, Gronemeyer H, De Lera AR (2006) Synthesis of the PPARβ/δ-selective agonist GW501516 and C4-thiazole-substituted analogs. Bioorg Med Chem Lett 16:49–54. doi:10.1016/j.bmcl.2005.09.060

    Article  CAS  Google Scholar 

  • Surendra K, Krishnaveni NS, Reddy MA, Nageswar YVD, Rao KR (2003) Highly selective oxidative cleavage of β-cyclodextrin-epoxide/aziridine complexes with IBX in water. J Org Chem 68:9119–9121. doi:10.1021/jo034079c

    Article  CAS  Google Scholar 

  • Tsuji K, Ishikawa H (1944) Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7. Biorg Med Chem Lett 4:1601–1606. doi:10.1016/S0960-894X(01)80574-6

    Article  Google Scholar 

  • Van Muijlwijk-Koezen JA, Timmerman H, Vollinga RC, DrabbeKunzel JF, De Groote M, Visser S, Ijzerman AP (2001) Thiazole and thiadiazole analogues as a novel class of adenosine receptor antagonists. Med Chem 44:749. doi:10.1021/jm0003945

    Article  Google Scholar 

  • Wagare DS, Farooqui M, Keche T, Durrani A (2016) Efficient and green microwave-assisted one-pot synthesis of azaindolizines in PEG-400 and water. Synth Commun 46:1741–1746. doi:10.1080/00397911.2016.1223314

    Article  CAS  Google Scholar 

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Acknowledgements

We are thankful to the UGC, New Delhi, for providing financial assistance under CPE-phase-II scheme and Principal, Vivekanand College, Aurangabad, to supporting this research work by providing the infrastructure at college central research facility.

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Authors and Affiliations

  1. Department of Chemistry, Vivekanand College, Aurangabad, MH, 431001, India

    Devendra S. Wagare

  2. Department of Chemistry, Maulana Azad College, Aurangabad, MH, 431001, India

    Prashant D. Netankar

  3. Department of Chemistry, Rafiq Zakaria College for Women, Aurangabad, MH, 431001, India

    Mujahed Shaikh, Mazahar Farooqui & Ayesha Durrani

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  1. Devendra S. Wagare
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  2. Prashant D. Netankar
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  3. Mujahed Shaikh
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  5. Ayesha Durrani
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Correspondence to Devendra S. Wagare.

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Wagare, D.S., Netankar, P.D., Shaikh, M. et al. Highly efficient microwave-assisted one-pot synthesis of 4-aryl-2-aminothiazoles in aqueous medium. Environ Chem Lett 15, 475–479 (2017). https://doi.org/10.1007/s10311-017-0619-1

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