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N-Methylimidazole-promoted efficient synthesis of 1,3-oxazine-4-thiones under solvent-free conditions

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Abstract

A novel method for oxazine ring formation is established using the reaction of ammonium thiocyanate and acid chlorides with napthols in the presence of N-methylimidazole to afford [1,3]oxazine-4-thione derivatives in excellent yields.

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References

  1. Krantz A, Spencer WR, Tam FT, Liak JT, Copp JL, Thomas ME, Rafferty PS (1990) J Med Chem 33:464

    Article  CAS  Google Scholar 

  2. Gutschow M, Kuerschner L, Neumann U, Pietsch M, Loser R, Koglin N, Eger K (1999) J Med Chem 42:5437

    Article  CAS  Google Scholar 

  3. Hsieh WP, Chang RF, Chang HC, Cheng WP, Chiang CL, Zeng LF, Lin KH, Wu CY (2004) Bioorg Med Chem Lett 14:4751

    Article  CAS  Google Scholar 

  4. Gutschow M, Neumann U (1997) Bioorg Med Chem 5:1935

    Article  CAS  Google Scholar 

  5. Brown DA, Powers CJ (1995) Bioorg Med Chem 3:1091

    Article  CAS  Google Scholar 

  6. Kern JC, Terefenko EA, Fensome A, Unwalla R, Wrobel J, Zhu Y, Cohen J, Winneker R, Zhang Z, Zhang P (2007) Bioorg Med Chem Lett 17:189

    Article  CAS  Google Scholar 

  7. Bolognese A, Correale G, Manfra M, Lavecchia A, Mazzoni O, Novellino E, Barone V, La Colla P, Loddo R (2002) J Med Chem 45:5217

    Article  CAS  Google Scholar 

  8. Jarvest RL, Connor SC, Gorniak JG, Jennings LJ, Serafinowska HT, West A (1997) Bioorg Med Chem Lett 7:1733

    Article  CAS  Google Scholar 

  9. Abood NA, Schretzman LA, Flynn DL, Houseman KA, Wittwer AJ, Dilworth VM, Hippenmeyer PJ, Holwerda BC (1997) Bioorg Med Chem Lett 7:2105

    Article  CAS  Google Scholar 

  10. Hsieh PW, Hwang TL, Wu CC, Chang FR, Wang TW, Wu YC (2005) Bioorg Med Chem Lett 15:2786

    Article  CAS  Google Scholar 

  11. Waisser K, Gregor J, Kubikova L, Klimesova V, Kunes J, Machacek M, Kaustova J (2000) Eur J Med Chem 35:733

    Article  CAS  Google Scholar 

  12. Waisser K, Kubicova L, Kaustova J, Bartsch H, Erker T, Hanus V (1999) Sci Pharm 67:123

    CAS  Google Scholar 

  13. Waisser K, Gregor J, Dostal H, Kunes J, Kubikova L, Klimesova V, Kaustova J (2001) farmaco 56:803

    Article  CAS  Google Scholar 

  14. Madhavan GR, Chakrabarti R, Reddy KA, Rajesh BM, Balaju V, Rao PB, Rajagopalan R, Iqbal J (2006) Bioorg Med Chem 14:584

    Article  CAS  Google Scholar 

  15. Colson E, Wallach J, Hauteville M (2005) Biochimie 87:223

    Article  CAS  Google Scholar 

  16. Atkinson PJ, Bromidge SM, Duxon MS, Gaster LM, Hadley MS, Hammond B, Johnson CN, Middlemiss DN, North SE, Price GW, Rami HK, Riley GJ, Scott CM, Shaw TE, Starr KR, Stemp G, Thewlis KM, Thomas DR, Thompson M, Vong AKK, Watson JM (2005) Bioorg Med Chem Lett 15:737

    Article  CAS  Google Scholar 

  17. Yavari I, Djahaniani H (2006) Tetrahedron Lett 47:2953

    Article  CAS  Google Scholar 

  18. Yavari I, Moradi L (2006) Helv Chim Acta 89:1942

    Article  CAS  Google Scholar 

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Acknowledgments

Financial support of this work from the Research Council of Qaemshahr Azad University is gratefully acknowledged.

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Authors and Affiliations

  1. Chemistry Department, Islamic Azad University, PO Box 163, Qaemshahr, Iran

    Mohammad A. Khalilzadeh, Zinatossadat Hossaini & Hasan Sadeghifar

  2. Chemistry Department, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

    Issa Yavari

Authors
  1. Mohammad A. Khalilzadeh
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  2. Issa Yavari
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  3. Zinatossadat Hossaini
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  4. Hasan Sadeghifar
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Correspondence to Mohammad A. Khalilzadeh.

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Khalilzadeh, M.A., Yavari, I., Hossaini, Z. et al. N-Methylimidazole-promoted efficient synthesis of 1,3-oxazine-4-thiones under solvent-free conditions. Monatsh Chem 140, 467–471 (2009). https://doi.org/10.1007/s00706-008-0042-1

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  • DOI: https://doi.org/10.1007/s00706-008-0042-1

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