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A simple synthesis of E-9-aryl-5-arylidene-1-oxo-1,2,3,4,5,6,7, 8-octahydroxanthenes and their lower analogues from E,E-α,α′-diarylidenecycloalkanones

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Abstract

A simple and efficient synthesis of E-9-aryl-5-arylidene-1-oxo-1,2,3,4,5,6,7,8-octahydroxanthenes and their lower analogues has been developed by amberlyst–15 catalysed cyclocondensation of E,E-α,α′-diarylidenecyclohexanones and E,E-α,α′-diarylidenecyclopentanones, respectively, with cyclohexan-1,3-diones. The products were obtained in moderate to good yield and their structures were confirmed from analytical and spectral data.

A simple and efficient synthesis of E-9-aryl-5-arylidene-1-oxo-1,2,3,4,5,6,7,8-octahydroxanthenes and their lower analogues has been developed by amberlyst-15 catalysed cyclocondensation of E,E-α,α′-diarylidenecyclohexanones and E,E-α,α′-diarylidenecyclopentanones, respectively, with cyclohexan-1,3-diones in anhydrous acetonitrile.

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References

  1. Lambert R W, Martin J A, Merrett J H, Parkes K E B and Thomas G J 1997 PCT Int. Appl. WO9706178, 1997 Chem. Abstr. 126 p212377y

  2. Hideo T 1981 Tokkyo Koho Jpn. JP 56005480, 1981 Chem. Abstr. 95 80922b

  3. Poupelin J P, Saint-Rut G, Fussard-Blanpin O, Narcisse G, Uchida-Ernouf G and Lakroix R 1978 Eur. J. Med. Chem. 13 67

    CAS  Google Scholar 

  4. Llama E F, Campo C B, Campo M and Anadon M 1989 Eur. J. Med. Chem. 24 391

    Article  CAS  Google Scholar 

  5. Chibale K, Visser M, Schalkwyk D V, Smith P J, Saravanamuthu A and Fairlamb A H 2003 Tetrahedron 59 2289

    Article  CAS  Google Scholar 

  6. (a) Cingolant G M and Pigini M 1988 J. Med. Chem. 12 531; (b) Hatakeyma S, Ochi N, Numata H and Takano S 1988 J. Chem. Soc., Chem. Commun. 24 1202

  7. (a) Arnone A, Merlini L and Nasini G 1972 Tetrahedron Lett. 13 3503; (b) Ravindranath B and Sheshadri T R 1973 Phytochemistry 12 2781; (c) Kinjo J, Uemura H, Nohara T, Yamashita N, Marubayashi N and Yoshihira K 1995 Tetrahedron Lett. 36 5599

  8. Banerjee A and Mukherjee A K 1981 Stain Technol. 56 83

    CAS  Google Scholar 

  9. (a) Bekaert A, Andrieux J and Plat M 1992 Tetrahedron Lett. 33 2805; (b) Sarma R J and Baruah J B 2005 Dyes Pigm. 64 91; (c) Buehler C A, Cooper D E and Scrudder E O 1943 J. Org. Chem. 8 316; (d) Knight C G and Stephens T 1989 Biochem. J. 258 683

  10. (a) Menchen S M, Benson S C, Lam J Y L, Zhen W, Sun D, Rosenblum B B, Khan S H and Taing M 2003 US Patent, US6583168, 2003 Chem. Abstr. 139 p54287f; (b) Sirkecioglu O, Tulinli N and Akar A, 1995 J. Chem. Res. (S) 1995 502

  11. (a) Ion R M, Frackowiak D, Planner A and Wiktorowicz K 1998 Acta Biochim. Pol. 45 833; (b) Ion R M 1997 Prog. Catal. 6 55

  12. (a) Hamada Y, Matsuura F, Oku M, Hatano K and Shioiri T 1997 Tetrahedron Lett. 38 8961; (b) Hillebrand S, Bruckmann J, Kruger C and Haenel M W 1995 Tetrahedron Lett. 36 75; (c) Malaise G, Barloy L and Osborn J A 2001 Tetrahedron Lett. 42 7417

  13. Few recent references: (a) Rashedian F, Saberi D and Niknam K 2010 J. Chin. Chem. Soc. 57 99; (b) Oskooie H A, Tahershamsi L, Heravi M M and Baghernejad B 2010 E-J. Chem. 7 717; (c) Mahdavinia G H, Ghanbari M M, Sepehrian H and Kooti F 2010 J. Iranian Chem. Res. 3 117; (d) Ali J, Majid M H and Fatemeh F B 2011 E-J. Chem. 8 910; (e) Pramanik A and Bhar S 2012 Catal. Commun. 20 17

  14. (a) Jiao C, Jian S and Chao-guo Y 2011 Chem. Res. Chin. Univ. 27 49; (b) Lasemi Z and Mehrasbi E, 1st National Iranian New Chemistry Congress 5–6 May, 2011, Shiraz

  15. Wang J, Han G, Wu X, Yin J and Zhao Y 2003 Chin. J. Org. Chem. 23 827

    CAS  Google Scholar 

  16. Tahmassebi D, Bryson, J A and Binz S I 2011 Synth. Commun. 41 2701

    Article  CAS  Google Scholar 

  17. (a) Pal R, Mandal T K, Guha C and Mallik A K 2011 J. Indian Chem. Soc. 88 711; (b) Mandal T K, Pal R, Mondal R and Mallik A K 2011 E- J. Chem. 8 863

  18. (a) Mallik A K, Pal R and Mandal T K 2007 Indian J. Chem. 46B 2056; (b) Pal R, Mandal T K and Mallik A K 2009 J. Indian Chem. Soc. 86 402; (c) Pal R, Mandal T K, Samanta S and Mallik A K 2010 J. Indian Chem. Soc. 87 711

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Acknowledgements

Financial assistance from the UGC-CAS and DST-PURSE programs, Department of Chemistry is gratefully acknowledged. The authors also acknowledge the DST-FIST program to the Department of Chemistry, Jadavpur University and Prof. D Mal, Department of Chemistry, Indian Institute of Technology (IIT), Kharagpur for providing the NMR spectral data. SS and AD are thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi and RM to the University Grants Commission (UGC), New Delhi for their Research Fellowships.

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Correspondence to ASOK K MALLIK.

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SAMANTA, S., GUPTA, A.D., MONDAL, R. et al. A simple synthesis of E-9-aryl-5-arylidene-1-oxo-1,2,3,4,5,6,7, 8-octahydroxanthenes and their lower analogues from E,E-α,α′-diarylidenecycloalkanones. J Chem Sci 125, 737–743 (2013). https://doi.org/10.1007/s12039-013-0442-6

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