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Amberlyst A-15: Reusable catalyst for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1H-imidazoles under MW irradiation

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Abstract

One-pot multi-component condensation of benzyl, aldehydes, ammonium acetate and primary amines were used for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1H-imidazole derivatives under MW radiation using amberlyst A-15 as a catalysts. This catalyst has several advantages (simple work-up, low cost and reusability).

One pot multi-component condensation of benzil, aldehydes, ammonium acetate and aromatic amine were used for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1H-imidazole derivatives repectively under MW irradation using Amberlyst A as a catalyst.

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References

  1. Sundberg R J and Martin R B 1974 Chem. Rev. 74 471

    Article  CAS  Google Scholar 

  2. (a) Bartlett M, Shaw M and Smith J W 1992 J. Med. Chem. Chim. Ther. 36 779; (b) Ghudamassi M, Barasent J, Imbach J and Gayral P 1988 Eup. J. Med. Chem. 23 225; (c) Hazelton J, Iddon B, Redhouse A D and Susehitzky H 1995 Tetrahedron 51 5597; (d) Lee J C, Llaydon J T, McDowell P C, Gallagher T T, Kumar S, Green D, Mckulty D, Blumenthal M, Heys J R, Landvaller S W, Strikler J H, Mclaughlin M M, Siemen I R, Fisher S M, Livi G P, White J R, Adams J L and P R Young 1994 Nature 372 739; (e) Lindberg P, Nordberg P, Alminger T, Brandstorm A and Wallmark B 1986 J. Med. Chem. 29 1327; (f) Koike H, Konse T, Sada T, Ikeda T, Hyogo A, Hinman D, Saito H and Yanigasawa H 2003 Ann. Rep. Sankyo Res. Lab. 55 1; (f) Leister C, Wang Y, Zhao Z and Lindsley C W 2004 Org. Lett. 6 1453; (g) Mannhold R 1985 Drugs Future 10 570

  3. (a) Sensui H, Ichikawa J and Sato S 1987 Japan Kokkai Tokyo Koho JP, 62 94 841: Chem Abstr. 107 187436q; (b) Satoru I 1989 Japan Kokkai Tokyo Koho JP 01117867 [89 117 867] Chem. Abst. 1989 111 214482

  4. Liebi R, Randte R, Mildenberger H, Bauer K and Bieringer H 1987 Chem. Abst. 108 6018 g

    Google Scholar 

  5. Wolkenberg S E, Wisnosk D D, Liester W B, Wang Y, Zhao Z and Lindsley C W 2004 Org. Lett. 6 1453

    Article  CAS  Google Scholar 

  6. Pozherskii A F, Soldalenkov A T and Katritzky A R 1997 Heterocycles in Life, Society; (New York: Wiley) 179

    Google Scholar 

  7. Lombardino J G and Wiseman E H 1974 J. Med. Chem. 17 1182

    Article  CAS  Google Scholar 

  8. Philips A P, White H L and Rosen S 1983 Eur. Pat. Appl. 1983, Eur. Pat. Appl. 58 890; Chem. Abst. 98 53894z

  9. Stocek V and Schunack W 1974 Arch. Pharmaz 307 922

    Article  Google Scholar 

  10. Davidson D, Weiss M and Jelling M 1937 J. Org. Chem. 2 319

    Article  CAS  Google Scholar 

  11. Stocek V and Schunack W 1976 Arch. Pharmaz 309 421; (b) Lipshutz B H and Morey M C 1983 J. Org. Chem. 48 3745

  12. Conssoni R, Croce P D, Ferraccioli R and Rosa 1991 J. Chem. Res. (s) 188

  13. (a) Schubert H and Stodolka J 1963 Prakt. Chem. 22 130; (b) Krieg B and Manccke G Z 1967 Naturforschung 222b 132

  14. (a) Evans D A and Lundy K M 1992 J. Am. Chem. Soc. 114 1495; (b) Schneiders P, Heinze J and Baumgartel H 1973 Chem. Ber. 106 2415

  15. Claiborne C F, Liverton N J and Nguyen K T 1998 Tetrahedron Lett. 39 8939

    Google Scholar 

  16. Grimett M R In Comprehensive Heterocyclic Chemistry II; Katritzky A R, Rees C W and Scriven E F 1996 E. F. V. Eds. (New York: Pergamon) Vol. 3 P77

  17. (a) Balalale S, Arabanian A and Hashtroudi M S 2000 Montash. Chem. 131 945; (b) Usyntinsky A Y and Khmelnitsky Y L 2000 Tetrahedron Lett. 41 5031

  18. (a) Abrumovitch R A 1991 Org. Proc. Pre. Int. 23 683; (b) Mingos D M P and Bughurst D R 1991 Chem. Soc. Rev. 201; (c) Caddick S 1995 Tetrahedron 51 10403; (d) Struee C R and Trainer R W 1995 Aust. J. Chem. 48 1665; (e) Loupy A, Petit A, Hamclin J, Texler-Boulter P, Jacquault P and Mathe D 1998 Synthesis 1213; (f) Verma R S 1999 Green Chem. 1 43; (g) Verma R S 1999 Clean Products Process 1 132; (h) Nalage S V, Kalyankar M B, Patil V S, Bhosale S V, Dehmukh S U and Pawar R P 2010 The Open Catalysis Journal 3 58; (i) Zhao N, Wang Y L and Wang J Y 2005 J. Chinese Chemical Society 52 535; (j) Fantini M, Zulini V, Spotti M A and Rivara M 2010 J. Combinatorial Chem. 12(1) 181; (k) Pathan M, Paike V V, Pachmase P R, More S P, Ardhapure S S and Pawar R P 2006 Arkivoc (XV) 205; (l) Shelke K, Kakade G, Shingate B and Shingare M 2008 Rasayan J. Chem. 1(3) 489; (m) Bratulescu G 2009 Synthesis 14 2319; (n) Gribble G W and Joule J A 2009 Progress in Heterocyclic Chemistry, Elsevier, Page No. 232–233; (o) El. Ashry E S H, Rashed N, Awad L F, Ramadan E, Abdel-Maggeed S M and Rezki N 2007 Arkivoc (VII) 30; (p) El-Shaieb K M 2006 Heteroatom Chem. 17(5) 365

  19. (a) Balalaie S, Hashem M M and Akhbari A 2003 Tetrahedron Lett. 44 (8) 1709; (b) Wassennan H H, Long Y O, Zhang R and Parr J 2002 Tetrahedron Lett. 43 3351; (c) Kamitori Y J 2001 Heterocycl. Chem. 38 773; (d) Kidwai M, Saxena S, Venkatraman R and Mohan R R 2002 J. C. S. Perkin Trans. I, 16 1845; (e) Kidwai M, and Mohan R R 2004 Canadian J. Chem. 82 427; (f) Kidwai M, Mothsra P, Bansal V and Goyal R 2006 Monatshefte Fur Chemie 137 1189; (g) Shaabani A, Rahmati A, Farhangi E and Badri Z 2007 Catalysis Communication 1149; (h) Balalie S and Arabanian A 2000 Green Chemistry 2 274; (i) Weiss M 1952 J. Org. Chem. 74 5193; (j) Xu Y, Wan L F, Salchi H, Deng W and Gua O X 2004 Heterocycles 63 1613; (k) Adib M, Ansari S, Feizi S, Damavandi J A and Mirzaei P 2009 Synlett. 3263; (l) Zuliani V, Cocconcelli G, Fantini M, Ghiron C and Rivara M 2007 J. Org. Chem. 72 4551; (m) Siddiqui S A, Narkhede U C, Palimkar S S, Daniel T, Lahoti R J and Srinivasan K V 2005 Tetrahedron 61 3539; (n) Safari J, Khalili S D and Banitaba S H 2010 J. Chem. Sci. 122(3) 347; (o) Arshia P, Azim A and Shaikh K A 2010 Research Journal of Pharmaceutical, Biological and Chemical Sciences 1(4) 943; (p) Baroniya S, Anwar Z, Sharma P K, Dudhe R and Kumar N 2010 1(3) 172; (q) Wang M, Gao J and Song Z 2010 Preparative Biochemistry and Biotechnology 40(4) 347

  20. (a) Whiten D M and Sonnenberg B 1964 J. Org. Chem. 29 1926; (b) Schubert H and Stodalka H 1963 J. Pract. Chem. 22 130; (c) Venkat Narsaiah A, Reddy A R, Reddy B V S and Yadav J S 2011 The Open Catalysis Journal 4 43; (d) Pavan Kumar C N S S, Shrinivas C, Sadhu P S, Rao V J and Palaniappan S 2009 J. Heterocyclic Chem. 46(5) 997; (e) Liu Y H, Liu Q S and Zhang Z H 2008 J. Molecular Catalysis A: Chemical 296 42; (f) Tajbakhsh M, Heydari Akbar, Khalilzadeh M A Lakouraj M M, Zamenian B and Khaksar S 2007 Synlett. 15 2347; (g) Tajbakhsh M, Hosseinzadeh R and Lasemi Z 2004 Synlett. 4 635

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Authors and Affiliations

  1. Post Graduate and Research Centre, Department of Chemistry, Padmashri Vikhe Patil College Pravaranagar (Loni Kd), Ahmednagar, 413 713, India

    SHIVAJI S PANDIT, SWAPNIL K BHALERAO, UDDHAV S AHER & GORAKSHANATH L ADHAV

  2. Post Graduate and Research Centre, Department of Chemistry, Fergusson College Pune, Pune, 411 004, India

    VIKRAM U PANDIT

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  1. SHIVAJI S PANDIT
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  2. SWAPNIL K BHALERAO
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  3. UDDHAV S AHER
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  4. GORAKSHANATH L ADHAV
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PANDIT, S.S., BHALERAO, S.K., AHER, U.S. et al. Amberlyst A-15: Reusable catalyst for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1H-imidazoles under MW irradiation. J Chem Sci 123, 421–426 (2011). https://doi.org/10.1007/s12039-011-0097-0

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  • DOI: https://doi.org/10.1007/s12039-011-0097-0

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