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Functionalization of Indole and Pyrrole Cores via Michael-Type Additions

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Bioactive Heterocycles V

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 11))

Abstract

The Michael reaction has been the subject of numerous reviews. Furthermore, the first review on anti-Michael addition has been published. The present review focuses only on the functionalization of indoles and the pyrroles via Michael additions because of the potential biological activity exhibited by these compounds.

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References

  1. O'Hagan D (2000) Nat Prod Rep 17:435

    Google Scholar 

  2. Black D StC (1996) In: Bird CW (ed) Comprehensive heterocyclic chemistry II, vol 2. Elsevier, Oxford UK, p 39

    Google Scholar 

  3. Banwell M, Goodwin TE, Ng S, Smith JA, Wong DJ (2006) Eur J Org Chem 3043

    Google Scholar 

  4. Hesse M (1974) Indolalkaloide. Verlag Chemie, Weinheim

    Google Scholar 

  5. Sundberg RJ (1970) In: Blomquist AT (ed) The chemistry of indoles. Academic, New York

    Google Scholar 

  6. Remers WA (1973) In: Houlihan WJ (ed) The chemistry of heterocyclic compounds, vol 25, chap 1. Wiley, New York

    Google Scholar 

  7. Bosch J, Luisa Bennasar M-L, Amat M (1996) Pure Appl Chem 68:557

    CAS  Google Scholar 

  8. Hibino S, Choshi T (2001) Nat Prod Rep 18:66

    CAS  Google Scholar 

  9. Knölker H-J, Reddy KR (2002) Chem Rev 102:4303

    Google Scholar 

  10. Banwell M, Edwards A, Smith J, Hamel E, Verdier-Pinard P (2000) J Chem Soc Perkin Trans I p 1497

    Google Scholar 

  11. Baudoin O, Cesario M, Guenard D, Gueritte F (2002) J Org Chem 67:1199

    CAS  Google Scholar 

  12. Abraham DJ, Rosenstein RD (1972) Tetrahedron Lett 13:909

    Google Scholar 

  13. De Silva KT, Ratcliffe AH, Smith GF, Smith GN (1972) Tetrahedron Lett 13:913

    Google Scholar 

  14. Banwell M, Smith J (2002) J Chem Soc Perkin Trans I, p 2613

    Google Scholar 

  15. Joule JA, Mills K, Smith GF (eds) (1995) Heterocyclic chemistry, 3rd edn. Chapman and Hall, London

    Google Scholar 

  16. Speeter ME, Anthony WC (1954) J Am Chem Soc 76:6208

    CAS  Google Scholar 

  17. Noble RL, Beer CT, Cutts JH (1958) Acad Sci 76:882

    CAS  Google Scholar 

  18. Yokoshima S, Ueda T, Kobayashi S, Sato A, Kuboyama T, Tokuyama H, Fukuyama T (2003) Pure Appl Chem 75:29

    CAS  Google Scholar 

  19. Chen ZH, Muller P, Swager TM (2006) Org Lett 8:273

    CAS  Google Scholar 

  20. Sha C-K (1996) Adv Nitrogen Heterocycl 2:147

    CAS  Google Scholar 

  21. LeHoullier CS, Gribble GW (1983) J Org Chem 48:2364

    CAS  Google Scholar 

  22. Bonnett R, North SA (1981) Adv Heterocycl Chem 29:341

    Article  CAS  Google Scholar 

  23. Chen Y-L, Lee M-H, Wong W-Y, Lee AWM (2006) Synlett, p 2510

    Google Scholar 

  24. Fleming I (1976) In: Frontier orbitals and organic chemical reactions. Wiley, New York, p 58

    Google Scholar 

  25. Fukui K, Yonezawa T, Nagata C, Shingu H (1954) J Chem Phys 22:1433

    CAS  Google Scholar 

  26. Bandini M, Melloni A, Umani-Ronchi A (2004) Angew Chem Int Ed 43:550

    CAS  Google Scholar 

  27. Bandini M, Melloni A, Tommasi S, Umani-Ronchi A (2005) Synlett, p 1199

    Google Scholar 

  28. Trost BM, Fleming I (eds) (1991) Comprehensive organic synthesis, vol 4. Pergamon, Oxford

    Google Scholar 

  29. Perlmutter P (1992) Conjugate addition reactions in organic synthesis. Pergamon, Oxford

    Google Scholar 

  30. Mukaiyama T, Kobayashi S (1994) Org React 46:1

    CAS  Google Scholar 

  31. Little RD, Masjedizadeh MR, Wallquist O, McLoughlin JI (1995) Org React 47:315

    CAS  Google Scholar 

  32. Johnson JS, Evan DA (2000) Acc Chem Res 33:325

    CAS  Google Scholar 

  33. Christoffers J (2001) Synlett, p 723

    Google Scholar 

  34. Leonard J (1994) Contemp Org Synth 1:387

    CAS  Google Scholar 

  35. Rossiter BE, Swingle NM (1992) Chem Rev 92:771

    CAS  Google Scholar 

  36. Lewandowska E (2006) Tetrahedron 63:2107

    Google Scholar 

  37. Wabnitz TC, Yu Q-J, Spencer JB (2004) Chem Eur J 10:484

    CAS  Google Scholar 

  38. Harrington PE, Kerr MA (1998) Can J Chem 76:1256

    CAS  Google Scholar 

  39. Harrington PE, Kerr MA (1996) Synlett, p 1047

    Google Scholar 

  40. Loh TP, Wei LL (1998) Synlett, p 975

    Google Scholar 

  41. Loh TP, Pei J, Lin M (1996) Chem Commun, p 2315

    Google Scholar 

  42. Babu G, Perumal PT (2000) Aldrichimica Acta 33:16

    CAS  Google Scholar 

  43. Yadav JS, Abraham S, Reddy BVS, Sabitha G (2001) Synthesis, p 2165

    Google Scholar 

  44. Bandini M, Melchiorre P, Melloni A, Umani-Ronchi A (2002) Synthesis, p 1110

    Google Scholar 

  45. Cox ED, Cook JM (1995) Chem Rev 95:1797

    CAS  Google Scholar 

  46. Cox ED, Diaz-Harauzo H, Huang Q, Reddy MS, Ma C, Harris B, McKernan R, Skolnick P, Cook JM (1998) J Med Chem 41:2537

    CAS  Google Scholar 

  47. Mobilio D, Humber LG, Katz AH, Demerson CA, Hughes P, Brigance R, Conway K, Shah U, Williams G, Labbadia F, De Lange B, Asselin A, Schmid J, Newburger J, Jensen NP, Weichman BM, Chau T, Neuman G, Wood DD, Van Engen D, Taylor N (1988) J Med Chem 31:2211

    CAS  Google Scholar 

  48. Humber LG (1987) Med Res Rev 7:1

    CAS  Google Scholar 

  49. Agnusdei M, Bandini M, Melloni A, Umani-Ronchi A (2003) J Org Chem 68:7126

    CAS  Google Scholar 

  50. Zhao S, Liao X, Cook JM (2002) Org Lett 4:687

    CAS  Google Scholar 

  51. Faulkner DJ (2001) J Nat Prod Rep 18:1

    CAS  Google Scholar 

  52. Miyake FY, Yakushijin K, Horne DA (2002) Org Lett 4:941

    CAS  Google Scholar 

  53. Jiang B, Yang C-G, Wang J (2002) J Org Chem 67:1396

    CAS  Google Scholar 

  54. Bandini M, Fagioli M, Melloni A, Umani-Ronchi A (2003) Synthesis, p 397

    Google Scholar 

  55. Bandini M, Cozzi PG, Giacomini M, Melchiorre P, Selva S, Umani-Ronchi A (2002) J Org Chem 67:3700

    CAS  Google Scholar 

  56. Arai K, Yamamoto Y (1990) Chem Pharm Bull 38:2929

    CAS  Google Scholar 

  57. Kaji A, Saito R, Nomura M, Miyamoto K, Kiryama N (1998) Biol Pharm Bull 21:945

    CAS  Google Scholar 

  58. Kaji A, Saito R, Hata Y, Kiriyama N (1999) Chem Pharm Bull 47:77

    CAS  Google Scholar 

  59. Kaji A, Iwata T, Kiriyama N, Wakusawa S, Miyamoto K (1994) Chem Pharm Bull 42:1682

    CAS  Google Scholar 

  60. Alvi KA, Pu H, Luche M, Rice A, App H, McMahon G, Dare H, Margolis B (1999) J Antibiot 52:215

    CAS  Google Scholar 

  61. Kaji A, Saito R, Nomura M, Miyamoto K, Kiriyama N (1997) Anticancer Res 17:3675

    CAS  Google Scholar 

  62. Zhang B, Salituro G, Szalkowski D, Li Z, Zhang Y, Royo I, Vilella D, Diez MT, Pelaez F, Ruby C, Kendall RL, Mao X, Griffin P, Calaycay J, Zierath JR, Heck JV, Smith RG, Moller DE (1999) Science 284:794

    Google Scholar 

  63. Yadav JS, Reddy BVS, Swamy T (2004) Synthesis, p 106

    Google Scholar 

  64. Lopez-Alvarado P, Alonso MA, Carmen A, Menendez JC (2001) Tetrahedron Lett 42:7971

    CAS  Google Scholar 

  65. Bartoli G, Bosco M, Giuli S, Giuliani A, Lucarelli L, Marcantoni E, Sambri L, Torregiani E (2005) J Org Chem 70:1941

    CAS  Google Scholar 

  66. Bartoli G, Bartolacci M, Bosco M, Foglia G, Giuliani A, Marcantoni E, Sambri L, Torregiani E (2003) J Org Chem 68:4594

    CAS  Google Scholar 

  67. Bandini M, Fagioli M, Umani-Ronchi A (2004) Adv Synth Catal 346:545

    CAS  Google Scholar 

  68. Alam MM, Varala R, Adapa SR (2003) Tetrahedron Lett 44:5115

    CAS  Google Scholar 

  69. Fiouzabadi H, Iranpoor N, Nowrouzi F (2005) Chem Commun, p 789

    Google Scholar 

  70. Li W-J, Lin X-F, Wang J, Li G-L, Wang Y-G (2005) Synlett, p 2003

    Google Scholar 

  71. Zhan Z-P, Yang R-F, Lang K (2005) Tetrahedron Lett 46:3859

    CAS  Google Scholar 

  72. Murugan R, Karthikeyan M, Perumal PT, Reddy BSR (2005) Tetrahedron 61:12275

    CAS  Google Scholar 

  73. Rajabi F, Saidi R (2005) J Sulf Chem 26:251

    CAS  Google Scholar 

  74. Fiouzabadi H, Iranpoor N, Jafari AA (2006) J Mol Catal A Chem, p 168

    Google Scholar 

  75. Tahir R, Banert K, Solhy A, Sebti S (2006) J Mol Catal A Chem, p 39

    Google Scholar 

  76. Singh DU, Singh PR, Samant SD (2006) Synth Commun 36:1265

    CAS  Google Scholar 

  77. Nayak SK (2006) Synth Commun 36:1307

    CAS  Google Scholar 

  78. Firouzabadi H, Iranpoor N, Jafarpour M, Ghaderi A (2006) J Mol Catal A Chem, p 150

    Google Scholar 

  79. Kumar V, Kaur S, Kumar S (2006) Tetrahedron Lett 47:7001

    CAS  Google Scholar 

  80. Arumugam P, Perumal P (2006) Chem Lett 35:632

    CAS  Google Scholar 

  81. Ye M-C, Yang Y-Y, Tang Y, Sun X-L, Ma Z, Qin W-M (2006) Synlett, p 1240

    Google Scholar 

  82. Srivastava N, Banik BK (2003) J Org Chem 68:2109

    CAS  Google Scholar 

  83. Cavdar H, Saracoglu N (2005) Tetrahedron 61:2401

    CAS  Google Scholar 

  84. Wang S-Y, Ji S-J, Loh T-P (2003) Synlett, p 2377

    Google Scholar 

  85. Banik BM, Fernandez M, Alvarez C (2005) Tetrahedron Lett 46:2479

    CAS  Google Scholar 

  86. Lin C, Hsu J, Sastry MNV, Fang H, Tu Z, Liu J-T, Ching-Fa Y (2005) Tetrahedron 61:11751

    CAS  Google Scholar 

  87. Ji S-J, Wang S-Y (2003) Synlett, p 2074

    Google Scholar 

  88. Ji S-J, Wang S-Y (2005) Ultrason Sonochem 12:339

    CAS  Google Scholar 

  89. Li J-T, Dai H-G, Xu W-Z, Li T-S (2006) J Chem Res, p 41

    Google Scholar 

  90. Quin LD (2000) A guide to organophosphorus chemistry. Wiley, New York

    Google Scholar 

  91. Corbridge DEC (1990) Phosphorus, an outline of its chemistry, biochemistry, and technology, 4th edn. Elsevier, Amsterdam

    Google Scholar 

  92. Yavari I, Norouzi-Arasi H (2002) Phosphor Sulfur Silicon Relat Elem 177:87

    CAS  Google Scholar 

  93. Krawczyk H, Sliwinski M (2002) Synthesis, p 1351

    Google Scholar 

  94. Couthon-Gourves H, Simon G, Haelters J-P, Corbel B (2006) Synthesis, p 81

    Google Scholar 

  95. Moran J, Suen T, Beauchemin AM (2006) J Org Chem 71:676

    CAS  Google Scholar 

  96. Kusurkar RS, Alkobati NAH, Gokule AS, Chaudhari PM, Waghchaure PB (2006) Synth Commun, p 1075

    Google Scholar 

  97. Jensen KB, Thorhauge J, Hazell RG, Jorgensen KA (2001) Angew Chem Int Ed 41:160

    Google Scholar 

  98. Zhuang W, Hansen T, Jorgensen KA (2001) Chem Commun, p 347

    Google Scholar 

  99. Palomo C, Oiarbide M, Kardak BG, Garcia JM, Linden A (2005) J Am Chem Soc 127:4154

    CAS  Google Scholar 

  100. Yamazaki S, Iwata Y (2006) J Org Chem 71:739

    CAS  Google Scholar 

  101. Zhou J, Tang Y (2004) Chem Commun, p 432

    Google Scholar 

  102. Jia Y-X, Zhu S-F, Yang Y, Zhou Q-L (2006) J Org Chem 71:75

    CAS  Google Scholar 

  103. Lu S-F, Du D-M, Xu J (2006) Org Lett 8:2115

    CAS  Google Scholar 

  104. Evans DA, Frandrick KR, Song H-J (2005) J Am Chem Soc 127:8942

    CAS  Google Scholar 

  105. Evans DA, Frandrick KR (2006) Org Lett 8:2249

    CAS  Google Scholar 

  106. Evans DA, Scheidt KA, Frandrick KR, Lam HW, Wu J (2003) J Am Chem Soc 125:10780

    CAS  Google Scholar 

  107. Zhou J, Tang Y (2002) J Am Chem Soc 124:9030

    CAS  Google Scholar 

  108. Zhou J, Ye M-C, Huang Z-Z, Tang Y (2004) J Org Chem 69:1309

    CAS  Google Scholar 

  109. Ye M-C, Li B, Zhou J, Sun X-L, Tang Y (2005) J Org Chem 70:6108

    CAS  Google Scholar 

  110. Austin JF, MacMillan DWC (2002) J Am Chem Soc 124:1172

    CAS  Google Scholar 

  111. Paras NA, MacMillan DWC (2002) J Am Chem Soc 124:7894

    CAS  Google Scholar 

  112. Taylor MS, Jacobsen EN (2003) J Am Chem Soc 125:11204

    CAS  Google Scholar 

  113. Bandini M, Fagioli M, Melchiorre P, Melloni A, Umani-Ronchi A (2003) Tetrahedron Lett 44:5843

    CAS  Google Scholar 

  114. Bandini M, Fagioli M, Garavelli M, Melloni A, Trigari V, Umani-Ronchi A (2004) J Org Chem 69:7511

    CAS  Google Scholar 

  115. Bandini M, Garelli A, Rovinetti M, Tommasi S, Umani-Ronchi A (2005) Chirality 17:522

    CAS  Google Scholar 

  116. Angeli M, Bandin M, Garell A, Piccinnell F, Tommas S, Umani-Ronch A (2006) Org Biomol Chem, p 3291

    Google Scholar 

  117. Bandini M, Melloni A, Tommasi S, Umani-Ronchi A (2003) Helv Chim Acta 86:3753

    CAS  Google Scholar 

  118. Herrera RP, Sgarzani V, Bernardi L, Ricci A (2005) Angew Chem Int Ed 44:6576

    CAS  Google Scholar 

  119. Fleming EM, McCabe T, Connon SJ (2006) Tetrahedron Lett 47:7037

    CAS  Google Scholar 

  120. Zhuang W, Hazell RG, Jorgensen KA (2005) Org Biomol Chem, p 2566

    Google Scholar 

  121. Sarstedt B, Winkerfeldt E (1983) Heterocycles 20:469

    CAS  Google Scholar 

  122. Hughes I, Raphael RA (1983) Tetrahedron Lett 24:1441

    CAS  Google Scholar 

  123. Magnus PD, Sear NL (1984) Tetrahedron 40:2795

    CAS  Google Scholar 

  124. Gribble GW, Berthel SJ (1992) Tetrahedron 48:8869

    CAS  Google Scholar 

  125. Bergman J, Pelcman B (2004) J Org Chem 69:7511

    Google Scholar 

  126. Kaneko T, Wong H, Okamoto KT, Clardy J (1985) Tetrahedron Lett 26:4015

    CAS  Google Scholar 

  127. Rahman A (ed) (1988) Studies in natural products chemistry. vol 1, Part A. Elsevier, Amsterdam

    Google Scholar 

  128. Kase H, Iwahashi K, Matsuda Y (1986) J Antibiot 39:1059

    CAS  Google Scholar 

  129. Sezaki M, Sasak T, Nakazaw T, Taked U, Iwat M, Watanab T, Koyam M, Ka F, Shomur T, Kojim M (1985) J Antibiot 38:1437

    CAS  Google Scholar 

  130. Hirayama N, Lida T, Shirahata K (1986) Acta Crystallogr 42:1402

    Google Scholar 

  131. Funato N, Takayanagi H, Konda Y, Toda Y, Harigaya Y, Iwai Y, Omura S (1994) Tetrahedron Lett 35:1251

    CAS  Google Scholar 

  132. Barry JF, Wallace TW, Walshe NDA (1993) Tetrahedron Lett 34:5329

    CAS  Google Scholar 

  133. Barry JF, Wallace TW, Walshe NDA (1995) Tetrahedron 51:12797

    CAS  Google Scholar 

  134. Link JT, Raghavan S, Danishefsky SJ (1995) J Am Chem Soc 117:552

    CAS  Google Scholar 

  135. Omura S, Iwai Y, Hirano A, Nakagawa A, Awaya J, Tsuchya H, Takahashi Y, Masuma R (1977) J Antibiot 30:275

    CAS  Google Scholar 

  136. Pindur U, Kim Y-S (1996) J Heterocycl Chem 33:623

    CAS  Google Scholar 

  137. Ikegami F, Murakoshi I (1994) Phytochemistry 5:1089

    Google Scholar 

  138. Dunnill M, Fowd L (1965) Phytochemistry 4:935

    Google Scholar 

  139. Shinozaki H, Konishi S (1974) Neuropharmacology 13:665

    CAS  Google Scholar 

  140. Evans RH, Francis AA, Hunt K, Martin MR, Watkins JC (1978) J Pharm Pharmac 30:364

    CAS  Google Scholar 

  141. lkegami F, Komada Y, Kobori M, Hawkins DR, Murakoshi I (1990) Phytochemistry 29:2507

    Google Scholar 

  142. Juaristi E (ed) (1997) Enantioselective synthesis of β-amino acids. Wiley, New York

    Google Scholar 

  143. Cardillo G, Tomasini C (1996) Chem Soc Rev 25:117

    CAS  Google Scholar 

  144. Shinagawa S, Kanamaru T, Harada S, Asai M, Okazaki M (1987) J Med Chem 30:1458

    CAS  Google Scholar 

  145. Kabawata N, Inamoto T, Hashimoto S (1992) J Antibiot 45:513

    Google Scholar 

  146. Matsuura F, Hamada Y, Shiouri T (1994) Tetrahedron 50:11303

    CAS  Google Scholar 

  147. Ferreira PMT, Maia HLS, Monteiro LS (1999) Tetrahedron Lett 40:4099

    CAS  Google Scholar 

  148. Huck J, Duru C, Roumestant ML, Martinez J (2003) Synthesis, p 2165

    Google Scholar 

  149. Rhodes CN, Brown DR (1993) J Chem Soc Faraday Trans 89:1387

    CAS  Google Scholar 

  150. Cativiela C, Figureras F, Garcia JI, Mayoral JA, Pires E, Royo AJ (1993) Tetrahedron: Asymmetry 4:621

    CAS  Google Scholar 

  151. Cativiela C, Fraile JM, Garcia JI, Mayoral JA, Pires E, Royo AJ, Figureras F (1993) Tetrahedron 43:4073

    Google Scholar 

  152. de la Hoz A, Diaz-Ortiz A, Gomez MV, Mayoral JA, Moreno A, Sanchez-Migallon AM, Vazquez E (2001) Tetrahedron 57:5428

    Google Scholar 

  153. Asselin AA, Humber LG, Voith K, Metcalf G (1986) J Med Chem 29:648

    CAS  Google Scholar 

  154. Nichols DE, Cassady JM, Persons PE, Yeung MC, Clemens JA, Smalstig EB (1989) J Med Chem 32:2128

    CAS  Google Scholar 

  155. Mewshaw RE, Marquis KL, Shi X, McGaughey G, Stack G, Webb MB, Abou-Gharbia M, Wasik T, Scerni R, Spangler T, Brennan JA, Mazandarani H, Coupet J, Andree TH (1998) Tetrahedron 54:7081

    CAS  Google Scholar 

  156. Daukshas VK, Martinkus RS, Gineitite VL, Urbonene SL (1982) Chem Heterocycl Compd (Engl Transl) 18:932

    Google Scholar 

  157. Ennis MD, Baze ME, Smith MW, Lawson CF, McCall RB, Lahti RA, Piercey MF (1992) J Med Chem 35:3058

    CAS  Google Scholar 

  158. Andrew M, Birch AM, Bradley PA (1999) Synthesis, p 1181

    Google Scholar 

  159. Partsvaniya DA, Akhvlediani RN, Zhigachev VE, Gordeev EN, Kuleshova LN, Suvorov NN, Vigdorchik MM, Mashkovskii MD (1986) Chem Heterocycl Compd (Engl Transl) 22:1311

    Google Scholar 

  160. Mayer S, Merour J-Y, Joseph B, Guillaumet G (2002) Eur J Org Chem, p 1646

    Google Scholar 

  161. Kebabian JW, Calne DB (1979) Nature (London) 277:93

    CAS  Google Scholar 

  162. Barnett A (1986) Drugs Fut 11:49

    Google Scholar 

  163. Setler PE, Sarau HM, Zirkle CL, Saunders HL (1978) Eur Pharmacol Sci 50:419

    CAS  Google Scholar 

  164. Kraxner J, Hübner H, Gmenier P (2000) Arch Pharm Pharm Med Chem 333:287

    CAS  Google Scholar 

  165. Yokoyama Y, Matsumoto T, Murakami Y (1995) J Org Chem 60:1486

    CAS  Google Scholar 

  166. Efange SMN, Mash DC, Khare AB, Quyang Q (1998) J Med Chem 41:4486

    CAS  Google Scholar 

  167. Gmeiner P, Sommer J, Höfner G (1995) Arc Pharm 328:329

    CAS  Google Scholar 

  168. Osawa T, Namiki M (1983) Tetrahedron Lett 24:4719

    CAS  Google Scholar 

  169. Fahy E, Potts BCM, Faulkner DJ, Smith K (1991) J Nat Prod 54:564

    CAS  Google Scholar 

  170. Bifulco G, Bruno I, Riccio R, Lavayre J, Bourdy G (1995) J Nat Prod 58:1254

    CAS  Google Scholar 

  171. Bell R, Carmeli S, Sar N (1994) J Nat Prod 57:1587

    CAS  Google Scholar 

  172. Garbe TR, Kobayashi M, Shimizu N, Takesue N, Ozawa M, Yukawa H (2000) J Nat Prod 63:596

    CAS  Google Scholar 

  173. Chakrabarty M, Basak R, Ghosh N (2001) Tetrahedron Lett 42:3913

    CAS  Google Scholar 

  174. Denis J-N, Mauger H, Valle'e Y (1997) Tetrahedron Lett 38:8515

    CAS  Google Scholar 

  175. Chalaye-Mauger H, Denis J-N, Averbuch-Pouchot M-T, Vallee Y (2000) Tetrahedron 56:791

    CAS  Google Scholar 

  176. Chakrabarty M, Basak R, Ghosh N, Harigaya Y (2004) Tetrahedron 60:1941

    CAS  Google Scholar 

  177. Spadoni G, Balsamini C, Bedini A, Duranti E, Tontini A (1992) J Heterocycl Chem 29:305

    CAS  Google Scholar 

  178. Bonjoch J, Sole D (2000) Chem Rev 100:3455

    CAS  Google Scholar 

  179. Ohshima T, Xu Y, Takita R, Shimizu S, Zhong D, Shibasaki M (2002) J Am Chem Soc 124:14546

    CAS  Google Scholar 

  180. Mori M, Nakanishi M, Kajishima DA, Sato Y (2003) J Am Chem Soc 125:9801

    CAS  Google Scholar 

  181. Gorman M, Neuss N, Biemann K (1962) J Am Chem Soc 84:1058

    CAS  Google Scholar 

  182. Moza BK, Trojanek J (1963) Collect Czech Chem Commun 28:1427

    CAS  Google Scholar 

  183. Buchi G, Matsumoto K, Nishimura H (1971) J Am Chem Soc 93:3299

    CAS  Google Scholar 

  184. Ando M, Buchi G, Ohnuma T (1975) J Am Chem Soc 97:6880

    CAS  Google Scholar 

  185. Heureux N, Wouters J, Marko IE (2005) Org Lett 7:5245

    CAS  Google Scholar 

  186. Hsu D-S, Rao PD, Liao C-C (1998) Chem Commun, p 1795

    Google Scholar 

  187. Rao PD, Chen C-H (1998) Chem Commun, p 155

    Google Scholar 

  188. Hsu P-Y, Lee Y-C, Liao C-C (1998) Tetrahedron Lett 39:659

    CAS  Google Scholar 

  189. Liu W-C, Liao C-C (1998) Synlett, p 912

    Google Scholar 

  190. Carlini R, Higgs K, Older C, Randhawa S, Rodrigo R (1997) J Org Chem 62:2330

    CAS  Google Scholar 

  191. Coleman RS, Grant EB (1995) J Am Chem Soc 117:10889

    CAS  Google Scholar 

  192. Hsieh M-F, Rao PD, Liao C-C (1999) Chem Commun, p 1441

    Google Scholar 

  193. Singh NB, Singh NP (1994) Tetrahedron 50:6441

    CAS  Google Scholar 

  194. Desiraju GR (ed) (1987) Organic solid state chemistry. Elsevier, Amsterdam

    Google Scholar 

  195. Toda F, Akai H (1990) J Org Chem 55:3446

    CAS  Google Scholar 

  196. Li X-L, Wang Y-M, Matsuura T, Meng J-B (1999) J Heterocycl Chem 36:697

    CAS  Google Scholar 

  197. Bodwell GJ, Li J, Miller OD (1999) Tetrahedron 55:12956

    Google Scholar 

  198. Wong DT, Bymaster FP, Engelman EA (1995) Life Sci 57:411

    CAS  Google Scholar 

  199. Brodfuehrer PR, Chen B, Sattleberg TR, Smith PR, Reddy JP, Stark DR, Quinlan SL, Reid JG, Thottathil JK, Wang S (1997) J Org Chem 62:9192

    CAS  Google Scholar 

  200. Denhart DJ, Mattson RJ, Ditta JL, Macor JE (2004) Tetrahedron Lett 45:3803

    CAS  Google Scholar 

  201. Belokon YN, Harutyunyan S, Vorontsov EV, Peregudov AS, Chrustalev VN, Kochetkov KA, Pripadchev D, Saygan AS, Beck AK, Seebach D (2004) ARKIVOC iii:132

    Google Scholar 

  202. Sabitha G, Kumar MR, Reddy MSK, Yadav JS, Krishna KVSR, Kunwar AC (2005) Tetrahedron Lett 46:1659

    CAS  Google Scholar 

  203. Pindur U (1988) Heterocycles 27:1253

    CAS  Google Scholar 

  204. Pindur U (1995) In: Moody CJ (ed) Advances in nitrogen heterocycles, vol 1. JAI, Greenwich, p 121

    Google Scholar 

  205. Sundberg R (1996) In: Meth-Cohn O (ed) Best synthetic methods, sub-series key systems and functional groups indoles. Academic, London

    Google Scholar 

  206. Saxton JE (ed) (1994) The chemistry of heterocyclic compounds, vol 25, Part IV. Wiley, Chichester

    Google Scholar 

  207. Macor JE (1990) Heterocycles 31:993

    CAS  Google Scholar 

  208. Madalengoitia JS, Macdonald TL (1993) Tetrahedron Lett 34:6237

    CAS  Google Scholar 

  209. Blechert S, Wirth T (1992) Tetrahedron Lett 33:6621

    CAS  Google Scholar 

  210. Wiest O, Steckhan E (1993) Angew Chem Int Ed Engl 32:901

    Google Scholar 

  211. Elango S, Srinivasan PC (1993) Tetrahedron Lett 34:1347

    CAS  Google Scholar 

  212. Balasubramanian T, Balasubramanian KK (1994) Chem Commun, p 1237

    Google Scholar 

  213. Dufour B, Motorina I, Fowler FW, Grierson DS (1994) Heterocycles 37:1455

    Article  CAS  Google Scholar 

  214. Rodriguez-Salvador L, Zaballos-Garcia E, Gonzalez-Rosende E, Sidi MD, Sepulveda-Arques J, Jones RA (1997) Synth Commun 27:1439

    CAS  Google Scholar 

  215. Joseph B, Da Costa H, Merour J-Y, Leonce S (2000) Tetrahedron 56:3189

    CAS  Google Scholar 

  216. Cavdar H, Saracoglu N (2006) J Org Chem 71:7793

    CAS  Google Scholar 

  217. Yadav JS, Abraham S, Reddy BVS, Sabitha G (2001) Tetrahedron Lett 42:8063

    CAS  Google Scholar 

  218. Zhan Z-P, Yang W-Z, Yang R-F (2005) Synlett, p 2425

    Google Scholar 

  219. Zhan Z-P, Yu J-L, Yang W-Z (2006) Synth Commun 36:1373

    CAS  Google Scholar 

  220. Zhang C-X, Wang Y-Q, Duan Y-S, Ge Z-M, Cheng T-M, Li R-T (2006) Catal Commun 7:534

    CAS  Google Scholar 

  221. Guida WC, Mathre DJJ (1980) Org Chem 45:3172

    CAS  Google Scholar 

  222. Hamaide T (1990) Synth Commun 20:2193

    Google Scholar 

  223. Wang N, Teo K, Anderson HJ (1977) Can J Chem 55:4112

    CAS  Google Scholar 

  224. Le Z-G, Chen Z-C, Hu Y, Zheng Q-G (2004) Synthesis, p 1951

    Google Scholar 

  225. Yang L, Xu L-W, Xia C-G (2005) Tetrahedron Lett 46:3279

    CAS  Google Scholar 

  226. Paras NA, MacMillan WC (2001) J Am Chem Soc 123:4370

    CAS  Google Scholar 

  227. Gordillo R, Carter J, Houk KN (2004) Adv Synth Catal 346:1175

    CAS  Google Scholar 

  228. Arroyo Y, de Paz M, Rodriguez JF, Sanz-Tejedor MA, Ruano JLG (2002) J Org Chem 67:5638

    CAS  Google Scholar 

  229. Rowan DD, Hunt MB, Gaynor DL (1986) J Chem Soc Chem Commun, p 935

    Google Scholar 

  230. Brimble MA (1990) J Chem Soc Perkin Trans I, p 311

    Google Scholar 

  231. Christophersen C (1985) In: Brossi A (ed) The alkaloids, vol 24. Academic, Orlando, chap 2

    Google Scholar 

  232. Umeyama A, Ito S, Yuasa E, Arihara S, Yamad T (1998) J Nat Prod 61:1433

    CAS  Google Scholar 

  233. Mancini I, Guella G, Amade P, Roussakis C, Pietra F (1997) Tetrahedron Lett 38:6271

    CAS  Google Scholar 

  234. Banwell MG, Bray AM, Wills AC, Wong D (1999) J New J Chem 23:687

    CAS  Google Scholar 

  235. Goh SH, Ali RMA, Wong WH (1989) Tetrahedron 45:7899

    CAS  Google Scholar 

  236. Banwell MG, Edwards AJ, Jolliffe KA, Smith JA, Hamel E (2003) Org Biomol Chem 296

    Google Scholar 

  237. Banwell MG, Beck DAS, Smith JA (2004) Org Biomol Chem 2:157

    CAS  Google Scholar 

  238. Banwell MG, Beck DAS, Willis AC (2006) ARKIVOC iii:163

    Google Scholar 

  239. Anderson HJ, Loader CE (1985) Synthesis, p 353

    Google Scholar 

  240. Hodges LM, Gonzalez J, Koontz JI, Myers WH, Harman WD (1993) J Org Chem 58:4788

    CAS  Google Scholar 

  241. Hodges LM, Gonzalez J, Koontz JI, Myers WH, Harman WD (1995) J Org Chem 60:2125

    CAS  Google Scholar 

  242. DuBois MR, Vasquez LD, Peslherbe L, Noll BC (1999) Organometallics 18:2230

    CAS  Google Scholar 

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Correspondence to Nurullah Saracoglu .

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Saracoglu, N. (2007). Functionalization of Indole and Pyrrole Cores via Michael-Type Additions. In: Khan, M.T.H. (eds) Bioactive Heterocycles V. Topics in Heterocyclic Chemistry, vol 11. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_073

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