Skip to main content

Preparation, Structure, and Biological Properties of Phosphorus Heterocycles with a C – P Ring System

  • Chapter
  • First Online:

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 8))

Abstract

Phosphoric acid esters, phosphates, have three P–O bonds around the central P(V) atom in the molecule. Replacing a phosphate P–O bond by a P–C bond and reducing the number of oxygen atoms one by one, converts phosphates into phosphonates, phosphinates, and phosphine oxides. Phospha sugar is a pseudo-sugar whose hemiacetal ring of the sugar contains a phosphorus atom with a C–P–C bond in the heterocycle, and is not yet found in nature. Research on phosphorus heterocycles is not as popular as that on nitrogen heterocycles, nevertheless the research is quite challenging.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Kandatsu M, Horiguchi M (1984) In: Hori T, Horiguchi M, Hayashi A (eds) Biochemistry of natural C–P compounds. Maruzen, Tokyo, chaps 1 and 6

    Google Scholar 

  2. Wong S-C, Carruthers NI, Chan T-M (1993) J Chem Res (S):268

    Google Scholar 

  3. Caesar JC, Griffiths DV (1987) Phosphor Sulf 29:123–127

    Article  CAS  Google Scholar 

  4. Quin LD, Tang J-S (1991) Heteroatom Chem 2(2):283–295

    Article  CAS  Google Scholar 

  5. Keglevich G, Toke L, Kovacs A, Toth G, Ujszaszy K (1993) Heteroatom Chem 4(1):61–72

    Article  CAS  Google Scholar 

  6. Kelevich G, Brlik J, Janke F, Toke L (1990) Heteroatom Chem 1(5):419–424

    Article  Google Scholar 

  7. Keglevich G, Quin LD (1995) Magyar Kemiai Folyoirat 101:282–292

    Google Scholar 

  8. Quin LD, Osman FH, Day Ro, Hughes AN, Wu XP, Wang LQ (1989) New J Chem 13:375–381

    CAS  Google Scholar 

  9. Keglevich G, Toke L, Kovacs A, Toth G, Ujszaszy K (1993) Heteroatom Chem 4(1):61–72

    Article  CAS  Google Scholar 

  10. Keglevich G, Kovacs A, Toke L, Ujszaszy K, Argay G, Czugler M, Kalman A (1993) Heteroatom Chem 4(4):329–335

    Article  CAS  Google Scholar 

  11. Keglevich G, Toke L, Lovasz C, Ujszaszy K, Szalontai G (1994) Heteroatom Chem 5(4):395–401

    Article  CAS  Google Scholar 

  12. Yamamoto H, Hanaya T, Kawamoto H, Inokawa S, Yamashita M, Armour M-A, Nakashima TT (1985) J Org Chem 50:3516

    Article  CAS  Google Scholar 

  13. Richter T, Luger P, Hanaya T, Yamamoto H (1989) Carbohydrate Res 193:9

    Article  CAS  Google Scholar 

  14. Hanaya T, Hirose K, Yamamoto H (1993) Heterocycles 36:2557

    Article  CAS  Google Scholar 

  15. Hanaya T, Yasuda K, Yamamoto H (1993) Bull Chem Soc Jpn 66:2315

    Article  CAS  Google Scholar 

  16. Hanaya T, Sugiyama K, Fujii Y, Akamatsu A, Yamamoto H (2001) Heterocycles 55(7):1301–1309

    Article  CAS  Google Scholar 

  17. Hanaya T, Yamamoto H (1989) Bull Chem Soc Jpn 62:2320

    Article  CAS  Google Scholar 

  18. Yamamoto H, Nakamura Y, Inokawa S, Yamashita M, Armour M-A, Nakashima TT (1984) J Org Chem 49:1364

    Article  CAS  Google Scholar 

  19. Hanaya T, Noguchi A, Armour M-A, Hogg AM, Yamamoto H (1992) J Chem Soc Perkin Trans 1, p 295

    Google Scholar 

  20. Hanaya T, Noguchi A, Yamamoto H (1991) Carbohydr Chem 209:C9

    Article  CAS  Google Scholar 

  21. Polniaszek RP, Foster AL (1991) J Org Chem 56:3137

    Article  CAS  Google Scholar 

  22. Yabui A, Yamashita M, Oshikawa T, Hanaya T, Yamamoto H (1995) Chem Lett, p 93

    Google Scholar 

  23. Hanaya T, Kawase S, Yamamoto H (2005) Heterocycles 66:251–261

    Article  CAS  Google Scholar 

  24. Baccolini G, Boga C, Negri U (2000) Synlett (11):1685–1687

    Google Scholar 

  25. Quin LD, Quin GS (2000) A guide to organophosphorus chemistry. Wiley-Interscience, New York

    Google Scholar 

  26. Dahl O, Edmundson RS (1996) In: Hartley FR (ed) The chemistry of organophosphorus compounds. Wiley, Chichester, chaps 1 and 2

    Google Scholar 

  27. Majoral J-P, Igau A, Cadierno V, Zablocka M (2002) In: Majoral J-P (ed) New aspects in phosphorus chemistry I. Springer, Berlin

    Chapter  Google Scholar 

  28. Reddy VK, Rao LN, Oshikawa T, Takahashi M, Yamashita M (2002) Phosphor Sulf Silicon 177:1801–1806

    Article  CAS  Google Scholar 

  29. Reddy VK, Onogawa J, Rao LN, Oshikawa T, Takahashi M, Yamashita M (2002) J Heterocycl Chem 39:69–75

    Article  CAS  Google Scholar 

  30. Yamashita M, Nakatsukasa Y, Yoshida H, Ogata T, Inokawa S, Hirotsu K, Clardy J (1979) Carbohydr Res 70:247–261

    Article  CAS  Google Scholar 

  31. Inokawa S, Yamamoto K, Kawata Y, Kawamoto H, Takagi K, Yamashita M (1980) Carbohydr Res 86:C11–12

    Article  CAS  Google Scholar 

  32. Yamashita M, Yamada M, Tsunekawa K, Oshikawa T, Seo K, Inokawa S (1983) Carbohydr Res 121:C4–C5

    Article  CAS  Google Scholar 

  33. Seo K, Yamashita M (1985) Carbohydr Res 141:335–339

    Article  CAS  Google Scholar 

  34. Emsley J, Hall D (1976) The chemistry of phosphorus. Harper & Row, London, p 157

    Google Scholar 

  35. Quin LD, Barket Tp (1967) J Chem Soc Chem Commun, p 288

    Google Scholar 

  36. McCormack WB (1963) Org Syn 43:73

    CAS  Google Scholar 

  37. Yamashita M, Uchimura M, Iida A, Parkanayi L, Clardy J (1988) J Chem Soc Chem Commun, pp 569–570

    Google Scholar 

  38. Yamashita M, Yabui A, Suzuki K, Kato Y, Uchimura M, Iida A, Mizuno H, Ikai K, Oshikawa T, Parkanayi L, Clardy J (1997) Carbohydr Res, pp 499–519

    Google Scholar 

  39. Yamashita M, Iida A, Ikai K, Oshikawa T, Hanaya T, Yamamoto H (1992) Chem Lett, pp 407–410

    Google Scholar 

  40. Ikai K, Iida A, Yamashita M (1989) J Syn Org Chem (8):595–597

    Google Scholar 

  41. Totsuka H, Maeda M, Reddy VK, Takahashi M, Yamashita M (2004) Heterocycl Commun 10(4–5):295–300

    CAS  Google Scholar 

  42. Miyamoto M, Yamashita M, Oshikawa T (1992) Bull Chem Soc Jpn 65(7):2004–2006

    Article  CAS  Google Scholar 

  43. Yamashita M, Suzuki K, Kato Y, Iida A, Ikai K, Reddy PM, Oshikawa T (1999) J Carbohydr Chem 18(8):915–935

    Article  CAS  Google Scholar 

  44. Yamashita M, Reddy VK, Rao LN, Haritha B, Maeda M, Suzuki K, Totsuka H, Takahashi M, Oshikawa T (2003) Tetrahedron Lett 44:2339–2341

    Article  CAS  Google Scholar 

  45. Totsuka H, Maeda M, Reddy VK, Takahashi M, Yamashita M (2004) Heterocycl Commun 10(4–5):295–300

    CAS  Google Scholar 

  46. Haritha B, Reddy VK, Oshikawa T, Yamashita M (2004) Tetrahedron Lett 45:1923–1927

    Article  CAS  Google Scholar 

  47. Yamashita M, Ikai K, Takahashi C, Oshikawa T (1993) Phosphor Sulf Silicon 79:293–296

    Article  CAS  Google Scholar 

  48. Yamashita M, Reddy PM, Kato Y, Reddy VK, Suzuki K, Oshikawa T (2001) Carbohydr Res 336:257–270

    Article  CAS  Google Scholar 

  49. Yamashita M, Reddy VK, Reddy PM, Kato Y, Haritha B, Suzuki K, Takahashi M, Oshikawa T (2003) Tetrahedron Lett 44:3455–3458

    Article  CAS  Google Scholar 

  50. Harith B, Reddy VK, Takahashi M, Yamashita M (2004) Tetrahedron Lett 45:5339–5341

    Article  CAS  Google Scholar 

  51. Bartret PA, Hanson JE, Giannousis PP (1990) J Org Chem 55:6268–6274

    Article  Google Scholar 

  52. Jacobsen NE, Bartlett PA (1981) J Am Chem Soc 103:654–657

    Article  CAS  Google Scholar 

  53. Yamashita M, Yamada M, Sugiura M, Nomoto H, Oshikawa T (1987) Nippon Kagaku Kaishi (7):1207–1213

    Google Scholar 

  54. Yamashita M, Fujie M, Nakamura S (2007) Japan patent application 2007-35083

    Google Scholar 

  55. Reddy VK, Rao LN, Maeda M, Haritha B, Yamashita M (2003) Heteroatom Chem 14(4):320–325

    Article  CAS  Google Scholar 

  56. Yamashita M, Rao LN, Reddy VK, Maeda M, Oshikawa T, Takahashi M (2002) Phosphor Sulf Silicon 177:1661–1665

    Article  CAS  Google Scholar 

  57. Yamashita M, Iida A, Oshikawa T, Kakehi A (1994) Chem Lett, pp 23–26

    Google Scholar 

  58. Yamashita M, Yabui A, Suzuki K, Kumagai S, Oshikawa T (1996) Phosphor Sulf Silicon 109–110:405–408

    Article  Google Scholar 

  59. Yamashita M, Yabui A, Oshikawa T, Hanaya T, Yamamoto H (1994) Heterocycles 38(7):1449–1452

    Article  CAS  Google Scholar 

  60. Yabui A, Yamashita M, Oshikawa T, Hanaya T, Yamamoto H (1993) Chem Lett, pp 93–96

    Google Scholar 

  61. Franisal N, Gallagher MJ (1987) Aust J Chem 40:1353–1363

    Article  CAS  Google Scholar 

  62. Kovacs J, Ire T, Ludanyi K, Toke L, Keglevich G (2004) Synth Commun 34(6):1033–1039

    Article  CAS  Google Scholar 

  63. Szelke H, Kovacs J, Keglevich G (2005) Synth Commun 35:2927–2934

    Article  CAS  Google Scholar 

  64. Natchev IA (1990) Bulgarian Acad Sci 23(4):511–515

    Google Scholar 

  65. Segall Y, Shirin E, Granoth I (1980) Phosphor Sulf 8:243–254

    Article  CAS  Google Scholar 

  66. Keglevich G, Thanh HTT, Ludanyi K, Novak T, Ujszaszy K, Toke L (1998) J Chem Res (S):210–211

    Google Scholar 

  67. Floch PL (2001) In: Mathey F (ed) Phosphorus–carbon heterocyclic chemistry: the rise of a new domain. Pergamon, Amsterdam, chap 5.2

    Google Scholar 

  68. Nyulaszi L (2001) Chem Rev 101:1229

    Article  CAS  Google Scholar 

  69. Mathey F (2003) Angew Chem Int Ed 42:1578

    Article  CAS  Google Scholar 

  70. de Koe P, Bickelhaupt F (2003) Z Naturforsh 58b:782–786

    Google Scholar 

  71. Murakami K, Shioda M, Kaji K, Yoshida S, Murofushi H (1992) J Biol Chem 267:21512–21517

    Google Scholar 

  72. Xu Y, Jiang G, Tsukahara R, Fujikawa Y, Tigyi G, Prestwich GD (2006) J Med Chem 49:5309–5315

    Article  CAS  Google Scholar 

  73. Quin LD, Osman FH, Day Ro, Hughes AN, Wu XP, Wang LQ (1989) New J Chem 13:375–381

    CAS  Google Scholar 

  74. Stoianova DS, Whitehead A, Hanson PR (2005) J Org Chem 70:5880–5889

    Article  CAS  Google Scholar 

  75. Hanaya T, Akamatsu A, Kawase S, Yamamoto H (1995) J Chem Res (S):194–195

    Google Scholar 

  76. Yamashita M, Niimi T, Fujie M, Reddy VK, Totsuka H, Haritha B, Reddy MK, Nakamura S, Asai K, Suyama T, Yu G, Takahashi M, Oshikawa T (2007) 17th International Conference on Phosphorus Chemistry (ICPC), Xiamen, China, 15–21 April 2007

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mitsuji Yamashita .

Editor information

Shoji Eguchi

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Yamashita, M. (2007). Preparation, Structure, and Biological Properties of Phosphorus Heterocycles with a C – P Ring System. In: Eguchi, S. (eds) Bioactive Heterocycles II. Topics in Heterocyclic Chemistry, vol 8. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_086

Download citation

Publish with us

Policies and ethics