Skip to main content

The Synthesis of Novel Dihydronaphthalenes and Benzofluorenes

  • Chapter
  • First Online:
Novel Selenium-Mediated Rearrangements and Cyclisations

Part of the book series: Springer Theses ((Springer Theses,volume 77))

  • 541 Accesses

Abstract

This chapter is concerned with the synthesis and applications of dihydronaphthalenes and benzofluorenes. This chapter describes literature methods for the preparation of dihydronaphthalenes and benzofluorenes. Efforts to discover new synthetic methods for the synthesis of dihydronaphthalenes and benzofluorenes are then described.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
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

Institutional subscriptions

References

  1. Sakakibara I, Ikeya Y, Hayashi K, Mitsuhashi H (1992) Phytochemistry 31:3219–3223

    Article  CAS  Google Scholar 

  2. Gonzalez AG, Aguiar ZE, Grillo TA, Luis JG (1992) Phytochemistry 31:1691–1695

    Article  CAS  Google Scholar 

  3. Haq Azhar-Ul, Malik A, Anis I, Khan SB, Ahmed E, Ahmed Z, Ahmad S, Nawaz SA, Choudhary MI (2004) Chem Pharm Bull 52:1269–1272

    Article  Google Scholar 

  4. Gennari L (2006) Lasofoxifene. Drugs Today 42:355–367

    Article  CAS  Google Scholar 

  5. Yang X, Reinhold AR, Rosati RL, Liu KK-C (2000) Org Lett 2:4025–4027

    Article  CAS  Google Scholar 

  6. Hejtmánková L, Jirman J, Sedlák M (2009) Res Chem Intermed 35:615–623

    Article  CAS  Google Scholar 

  7. Scribner AW, Haroutounian SA, Carlson KE, Katzenellenbogen JA (1997) J Org Chem 62:1043–1057

    Article  CAS  Google Scholar 

  8. Hutchinson DK, Rosenberg T, Klein LL, Bosse TD, Larson DP, He W, Jiang WW, Kati WM, Kohlbrenner WE, Liu Y, Masse SV, Middleton T, Molla A, Montgomery DA, Beno DWA, Stewart KD, Stoll VS, Kempf DJ (2008) Bioorg Med Chem Lett 18:3887–3890

    Article  CAS  Google Scholar 

  9. Voets M, Antes I, Scherer C, Müller-Vieira U, Biemel K, Marchais-Oberwinkler S, Hartmann RW (2006) J Med Chem 49:2222–2231

    Article  CAS  Google Scholar 

  10. Silva LF Jr, Siqueira FA, Pedrozo EC, Vieira FYM, Doriguetto AC (2007) Org Lett 9:1433–1436

    Article  CAS  Google Scholar 

  11. Inoue H, Chatani N, Murai S (2002) J Org Chem 67:1414–1417

    Article  CAS  Google Scholar 

  12. GowriSankar S, Lee CG, Kim JN (2004) Tetrahedron Lett 45:6949–6953

    Article  CAS  Google Scholar 

  13. Sil D, Ram VJ (2005) Tetrahedron Lett 46:5013–5015

    Article  CAS  Google Scholar 

  14. Pape AR, Kaliappan KP, Kündig EP (2000) Chem Rev 100:2917–2940

    Article  CAS  Google Scholar 

  15. Meyers AI, Brown JD (1987) Tetrahedron Lett 28:5279–5282

    Article  CAS  Google Scholar 

  16. Meyers AI, Lutomski KA, Laucher D (1988) Tetrahedron 44:3107–3118

    Article  CAS  Google Scholar 

  17. Tomioka K, Shindo M, Koga K (1990) Tetrahedron Lett 31:1739–1740

    Article  CAS  Google Scholar 

  18. Shindo M, Koga K, Asano Y, Tomioka K (1999) Tetrahedron 55:4955–4968

    Article  CAS  Google Scholar 

  19. Rao AVR, Yadav JS, Reddy KB, Mehendale AR (1984) Tetrahedron 40:4643–4647

    Article  Google Scholar 

  20. Ferraz HMC, Silva LF Jr, Vieira TO (2001) Tetrahedron 57:1709–1713

    Article  CAS  Google Scholar 

  21. Harrowven DC, Wilden JD, Tyte MJ, Hursthouse MB, Coles SJ (2001) Tetrahedron Lett 42:1193–1195

    Article  CAS  Google Scholar 

  22. Neudeck H, Brinker UH (2005) Tetrahedron Lett 46:1893–1895

    Article  CAS  Google Scholar 

  23. Davies HML, Jin Q (2005) Org Lett 7:2293–2296

    Article  CAS  Google Scholar 

  24. Davies HML, Dai X, Long MS (2006) J Am Chem Soc 128:2485–2490

    Article  CAS  Google Scholar 

  25. Silva LF Jr, Siqueira FA, Pedrozo EC, Vieira FYM, Doriguetto AC (2007) Org Lett 9:1433–1436

    Article  CAS  Google Scholar 

  26. Bianco GG, Ferraz HMC, Costa AM, Costa-Lotufo LV, Pessoa C, de Moraes MO, Schrems MG, Pfaltz A, Silva LF Jr (2009) J Org Chem 74:2561–2566

    Article  CAS  Google Scholar 

  27. Kündig EP, Desobry V, Simmons DP (1983) J Am Chem Soc 105:6962–6963

    Article  Google Scholar 

  28. Srikrishna AJ (1987) J Chem Soc Chem Comm :587–588

    Google Scholar 

  29. McMurry JE, Swenson R (1987) Tetrahedron Lett 28:3209–3212

    Article  CAS  Google Scholar 

  30. Nadeau E, Ventura DL, Brekan JA, Davies HML (2010) J Org Chem 75:1927–1939

    Article  CAS  Google Scholar 

  31. De B, DeBernardis JF, Prasad R (1988) Synth Comun 78:481–485

    Article  Google Scholar 

  32. Caldirola P, Ciancaglioni M, De Amici M, De Micheli C (1986) Tetrahedron Lett 27:4647–4650

    Article  CAS  Google Scholar 

  33. Linker T, Peters K, Peters E-M, Rebien F (1996) Angew Chem Int Ed Engl 35:2487–2489

    Article  CAS  Google Scholar 

  34. Lautens M, Fagnou K, Rovis T (2000) J Am Chem Soc 122:5650–5651

    Article  CAS  Google Scholar 

  35. Lautens M, Hiebert S (2004) J Am Chem Soc 126:1437–1447

    Article  CAS  Google Scholar 

  36. Miller JA (2002) Tetrahedron Lett 43:7111–7114

    Article  CAS  Google Scholar 

  37. Shi M, Wu L, Lu J-M (2008) J Org Chem 73:8344–8347

    Article  CAS  Google Scholar 

  38. Birch AJ, Subba Rao GSR (1972) Adv Org Chem 8:1–65

    CAS  Google Scholar 

  39. Rabideau PW, Karrick GL (1987) Tetrahedron Lett 28:2481–2484

    Article  CAS  Google Scholar 

  40. Subba Rao GSR, Shyama Sundar N (1982) J Chem Soc Perkin 1:875–880

    Google Scholar 

  41. Ochiai M, Takaoka Y, Sumi K, Nagaoa Y (1986) J Chem Soc, Chem Commun :1382–1384

    Google Scholar 

  42. Angle SR, Arnaiz DO (1991) Tetrahedron Lett 32:2327–2330

    Article  CAS  Google Scholar 

  43. Santi R, Bergamini F, Citterio A, Sebastiano R, Nicolini M (1992) J Org Chem 57:4250–4255

    Article  CAS  Google Scholar 

  44. Harrowven DC, Tyte MJ (2002) Tetrahedron Lett 43:5971–5972

    Article  CAS  Google Scholar 

  45. Hamura T, Miyamoto M, Imura K, Matsumoto T, Suzuki K (2002) Org Lett 4:1675–1678

    Article  CAS  Google Scholar 

  46. Asao N, Kasahara T, Yamamoto Y (2003) Angew Chem Int Ed 42:3504–3506

    Article  CAS  Google Scholar 

  47. Nishizawa M, Takao H, Yadav VK, Imagawa H, Sugihara T (2003) Org Lett 5:4563–4565

    Article  CAS  Google Scholar 

  48. Zhou H, Huang X, Chen W (2004) J Org Chem 69:5471–5472

    Article  CAS  Google Scholar 

  49. Wu M-S, Jeganmohan M, Cheng C-H (2005) J Org Chem 70:9545–9550

    Article  CAS  Google Scholar 

  50. Ichikawa J, Kaneko M, Yokota M, Itonaga M, Yokoyama T (2006) Org Lett 8:3167–3170

    Article  CAS  Google Scholar 

  51. Jiang Jia-Li, Jia Ju, Hua Ruimao (2007) Org Biomol Chem 5:1854–1857

    Article  CAS  Google Scholar 

  52. Zhao H, Vandenbossche CP, Koenig SG, Singh SP, Bakale RP (2008) Org Lett 10:505–507

    Article  CAS  Google Scholar 

  53. Huang W, Zheng P, Zhang Z, Liu R, Chen Z, Zhou X (2008) J Org Chem 73:6845–6848

    Article  CAS  Google Scholar 

  54. Lu S, Xu Z, Bao M, Yamamoto Y (2008) Angew Chem Int Ed 47:4366–4369

    Article  CAS  Google Scholar 

  55. Rayabarapu DK, Chiou C-F, Cheng C-H (2002) Org Lett 4:1679–1682

    Article  CAS  Google Scholar 

  56. Qiu Z, Xie Z (2009) Angew Chem Int Ed 48:5729–5732

    Article  CAS  Google Scholar 

  57. Fang X, Li C, Tong X (2009) Chem Commun :5311–5313

    Google Scholar 

  58. Hu Z-L, Qian W-J, Wang S, Wang S, Yao Z-J (2009) Org Lett 11:4676–4679

    Article  CAS  Google Scholar 

  59. Cho Y-h, Zunic V, Senboku H, Olsen M, Lautens M (2006) J Am Chem Soc 128:6837–6846

    Article  CAS  Google Scholar 

  60. Kurouchi H, Sugimoto H, Otani Y, Ohwada T (2010) J Am Chem Soc 132:807–815

    Article  CAS  Google Scholar 

  61. Ito S, Matsuya T, Omura S, Otani M, Nakagawa A (1970) J Antibiot 23:315–317

    Article  CAS  Google Scholar 

  62. Cone MC, Seaton PJ, Halley KA, Gould SJ (1989) J Antibiot 42:179–188

    Article  CAS  Google Scholar 

  63. Seaton PJ, Gould SJ (1989) J Antibiot 42:189–197

    Article  CAS  Google Scholar 

  64. Gould SJ, Chen J, Cone MC, Gore MP, Melville CR, Tamayo N (1996) J Org Chem 61:5720–5721

    Article  CAS  Google Scholar 

  65. Gould SJ, Tamayo N, Melville CR, Cone MC (1994) J Am Chem Soc 116:2207–2208

    Article  CAS  Google Scholar 

  66. Cone MC, Melville CR, Gore MP, Gould SJ (1993) J Org Chem 58:1058–1061

    Article  CAS  Google Scholar 

  67. Shin-ya K, Furihata K, Teshima Y, Hayakawa Y, Seto H (1992) Tetrahedron Lett 33:7025–7028

    Article  CAS  Google Scholar 

  68. Gould SJ, Melville CR (1995) Bioorg Med Chem Lett 5:51–54

    Article  CAS  Google Scholar 

  69. Carney JR, Hong A-T, Gould SJ (1997) Tetrahedron Lett 38:3139–3142

    Article  CAS  Google Scholar 

  70. Aoyama T, Zhao W, Kojima F, Muraoka Y, Naganawa H, Takeuchi T, Aoyagi T (1993) J Antibiot 46:1471–1474

    Article  CAS  Google Scholar 

  71. Gould SJ, Chen J, Cone MC, Gore MP, Melville CR, Tamaya N (1996) J Org Chem 61:5720–5721

    Article  CAS  Google Scholar 

  72. Gould SJ, Melville CR, Cone MC, Chen J, Carney JR (1997) J Org Chem 62:320–324

    Article  CAS  Google Scholar 

  73. Loozen HJJ, Wagener M, Veeneman GH, Zwart EW (2003).PCT Int Appl, WO 2003053994 or US patent 2008, 7335659B2

    Google Scholar 

  74. Kim K-S, Jeon Y-M, Lee H-S, Kim J-W, Lee C-W, Jang J-G, Gong M-S (2008) Syn Metals 158:870–875

    Article  CAS  Google Scholar 

  75. M-Contelles J, Molina TM (2003) Curr Org Chem 7:1433–1442

    Article  Google Scholar 

  76. Mal D, Hazra NK (1996) Tetrahedron Lett 37:2641–2642

    Article  CAS  Google Scholar 

  77. Chuang CP, Wang SF (1996). Synlett 829 − 830

    Google Scholar 

  78. Williams W, Sun X, Jebaratnam D (1997) J Org Chem 62:4364–4369

    Article  CAS  Google Scholar 

  79. Gore MP, Gould SJ, Weller DD (1992) J Org Chem 57:2774–2783

    Article  CAS  Google Scholar 

  80. Qabaja G, Jones GB (2000) J Org Chem 65:7187–7194

    Article  CAS  Google Scholar 

  81. Cantalapiedra EG, de Frutos O, Atienza C, Mateo C, Echavarren AM (2006) Eur J Org Chem :1430–1443

    Google Scholar 

  82. Hauser FM, Zhou M (1996) J Org Chem 61:5722

    Article  CAS  Google Scholar 

  83. Koyama H, Kamikawa T (1997) Tetrahedron Lett 38:3973–3976

    Article  CAS  Google Scholar 

  84. Koyama H, Kamikawa T (1998) J. Chem. Soc. Perkin Trans. 1:203–209

    Article  Google Scholar 

  85. Kumamoto T, Tabe N, Yamaguchi K, Ishikawa T (2000) Tetrahedron Lett 41:5693–5697

    Article  CAS  Google Scholar 

  86. Schmittel M, Strittmatter M, Vollmann K, Kiau S (1996) Tetrahedron Lett 37:999–1002

    Article  CAS  Google Scholar 

  87. Schmittel M, Keller M, Kiau S, Strittmatter M (1997) Chem Eur J 3:807–816

    Article  CAS  Google Scholar 

  88. Mohri S, Stefinovic M, Snieckus V (1997) Org Chem 62:7072–7073

    Article  CAS  Google Scholar 

  89. Rodriguez D, Castedo L, Dominguez D, Saá C (1999) Tetrahedron Lett 40:7701–7704

    Article  CAS  Google Scholar 

  90. Kawano T, Suehiro M, Ueda I (2006) Chem Lett 35:58–59

    Article  CAS  Google Scholar 

  91. Bestmann H (1980) J Pure Appl Chem 52:771–788

    Article  CAS  Google Scholar 

  92. Boehme R, Wilhelm E (1980) Cryst Struct Commun 9:933–936

    CAS  Google Scholar 

  93. Streitwieser A, Brown SM (1988) J Org Chem 53:904–906

    Article  CAS  Google Scholar 

  94. Mal D, Hazra NK (1996) Tetrahedron Lett 37:2641–2642

    Article  CAS  Google Scholar 

  95. Schmittel M, Strittmatter M, Kiau S (1996) Angew Chem Int Ed Engl 35:1843–1845

    Article  CAS  Google Scholar 

  96. de Frutos Ó, Echavarren AM (1997) Tetrahedron Lett 38:7941–7942

    Article  Google Scholar 

  97. Wang KK, Zhang H-R, Petersen JL (1999) J Org Chem 64:1650–1656

    Article  CAS  Google Scholar 

  98. Rodríguez D, Navarro A, Castedo L, Domínguez D, Saá C (2000) Org Lett 2:1497–1500

    Article  CAS  Google Scholar 

  99. Yang H, Petersen JL, Wang KK (2006) Tetrahedron 62:8133–8141

    Article  CAS  Google Scholar 

  100. Xu G-C, Liu L-P, Lu J-M, Shi M (2005) J Am Chem Soc 127:14552–14553

    Article  CAS  Google Scholar 

  101. Patra A, Ghorai SK, De SR, Mal D (2006) Synthesis 15:2556–2562

    Google Scholar 

  102. Birman VB, Zhao Z, Guo L (2007) Org Lett 9:1223–1225

    Article  CAS  Google Scholar 

  103. Guo L-N, Duan X-H, Liu X-Y, Hu J, Bi H-P, Liang Y-M (2007) Org Lett 9:5425–5428

    Article  CAS  Google Scholar 

  104. Xu X–X, Dong H-Q (1995) J Org Chem 60:3039–3044

    Article  CAS  Google Scholar 

  105. Dieck HA, Heck RF (1974) J Am Chem Soc 96:1133–1136

    Article  CAS  Google Scholar 

  106. Premasagar V, Palaniswamy VA, Eisenbraun EJ (1981) J Org Chem 46:2974–2976

    Article  CAS  Google Scholar 

  107. Firouzabadi H, Iranpoor N, Nowrouzi F (2004) Tetrahedron 60:10843–10850

    Article  CAS  Google Scholar 

  108. Zamayaki T, Urabe H, Sato F (1998) Bull Chem Soc Jpn 71:1673–1681

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sohail Anjum Shahzad .

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Shahzad, S.A. (2013). The Synthesis of Novel Dihydronaphthalenes and Benzofluorenes. In: Novel Selenium-Mediated Rearrangements and Cyclisations. Springer Theses, vol 77. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-33173-2_2

Download citation

Publish with us

Policies and ethics