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Biginelli Multicomponent Reactions in Polymer Science

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Book cover Multi-Component and Sequential Reactions in Polymer Synthesis

Part of the book series: Advances in Polymer Science ((POLYMER,volume 269))

Abstract

The Biginelli reaction, a three-component cyclocondensation reaction, is an important member of the multicomponent reaction (MCR) family. The Biginelli reaction is so efficient and shares many similar properties as the recent click reactions. In this chapter, we summarised the current applications of the Biginelli reaction in polymer chemistry including polymer coupling, post polymer modification, and new functional polymer synthesis. We expect this ‘old’ reaction (>120 years) can draw attention from polymer chemists and play new roles in the polymer science.

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References

  1. Tron GC, Minassi A, Appendino G (2011) Eur J Org Chem 2011:5541–5550

    CAS  Google Scholar 

  2. Aron ZD, Overman LE (2004) Chem Commun 2004:253–265

    Google Scholar 

  3. Kappe CO (2000) Acc Chem Res 33:879–888

    CAS  Google Scholar 

  4. Dharma Rao GB, Anjaneyulu B, Kaushik MP (2014) Tetrahedron Lett 55:19–22

    CAS  Google Scholar 

  5. Oliverio M, Costanzo P, Nardi M, Rivalta I, Procopio A (2014) ACS Sustainable Chem Eng 2:1228–1233

    CAS  Google Scholar 

  6. Kappe CO (2000) Eur J Med Chem 35:1043–1052

    CAS  Google Scholar 

  7. Sandhu JS (2012) Arkivoc 1:66–133

    Google Scholar 

  8. Sabitha G, Kiran Kumar Reddy GS, Reddy S, Yadav JS (2003) Synlett 2003:0858–0860

    Google Scholar 

  9. Bose AK, Manhas MS, Pednekar S, Ganguly SN, Dang H, He W, Mandadi A (2005) Tetrahedron Lett 46:1901–1903

    CAS  Google Scholar 

  10. Panda SS, Khanna P, Khanna L (2012) Curr Org Chem 16:507–520

    CAS  Google Scholar 

  11. Warekar PP, Kolekar GB, Deshmukh MB, Anbhule PV (2014) Synth Commun 44:3594–3601

    CAS  Google Scholar 

  12. Kappe CO (2003) QSAR Comb Sci 22:630–645

    CAS  Google Scholar 

  13. Stadler A, Kappe CO (2001) J Comb Chem 3:624–630

    CAS  Google Scholar 

  14. Sabitha G, Reddy GS, Reddy KB, Yadav JS (2003) Tetrahedron Lett 44:6497–6499

    CAS  Google Scholar 

  15. Khanetskyy B, Dallinger D, Kappe CO (2004) J Comb Chem 6:884–892

    CAS  Google Scholar 

  16. Wipf P, Cunningham A (1995) Tetrahedron Lett 36:7819–7822

    CAS  Google Scholar 

  17. Cushman M, Nagarathnam D, Burg DL, Geahlen RL (1991) J Med Chem 34:798–806

    CAS  Google Scholar 

  18. Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S, Gougoutas JZ, O’Reilly BC, Schwartz J, Malley MF (1992) J Med Chem 35:3254–3263

    CAS  Google Scholar 

  19. Patil AD, Kumar NV, Kokke WC, Bean MF, Freyer AJ, Brosse CD, Mai S, Truneh A, Carte B (1995) J Org Chem 60:1182–1188

    CAS  Google Scholar 

  20. Jadhav VB, Holla HV, Tekale SU, Pawar RP (2012) Der Chem Sin 3:1213–1228

    CAS  Google Scholar 

  21. Grover GJ, Dzwonczyk S, McMullen DM, Normandin DE, Parham CS, Sleph PG, Moreland S (1995) J Cardiovasc Pharmacol 26:289–294

    CAS  Google Scholar 

  22. Chikhale RV, Bhole RP, Khedekar PB, Bhusari KP (2009) Eur J Med Chem 44:3645–3653

    CAS  Google Scholar 

  23. Marvaniya HM, Parikh PK, Sen DJ (2011) J Appl Pharm Sci 1:109–113

    Google Scholar 

  24. Lewis RW, Mabry J, Polisar JG, Eagen KP, Ganem B, Hess GP (2010) Biochemistry 49:4841–4851

    CAS  Google Scholar 

  25. Trivedi AR, Bhuva VR, Dholariya BH, Dodiya DK, Kataria VB, Shah VH (2010) Bioorg Med Chem Lett 20:6100–6102

    CAS  Google Scholar 

  26. Chiang AN, Valderramos J-C, Balachandran R, Chovatiya RJ, Mead BP, Schneider C, Bell SL, Klein MG, Huryn DM, Chen XS, Day BW, Fidock DA, Wipf P, Brodsky JL (2009) Bioorg Med Chem Lett 17:1527–1533

    CAS  Google Scholar 

  27. Ravendra Babu K, Koteswara Rao V, Nanda Kumar Y, Polireddy K, Venkata Subbaiah K, Bhaskar M, Lokanatha V, Naga Raju C (2012) Antiviral Res 95:118–127

    CAS  Google Scholar 

  28. Deshmukh MB, Salunkhe SM, Patil DR, Anbhule PV (2009) Eur J Med Chem 44:2651–2654

    CAS  Google Scholar 

  29. Chitra S, Devanathan D, Pandiarajan K (2010) Eur J Med Chem 45:367–371

    CAS  Google Scholar 

  30. Tawfik HA, Bassyouni F, Gamal-Eldeen AM, Abo-Zeid MA, El-Hamouly WS (2009) Pharmacol Rep 61:1153–1162

    CAS  Google Scholar 

  31. Agbaje OC, Fadeyi OO, Fadeyi SA, Myles LE, Okoro CO (2011) Bioorg Med Chem Lett 21:989–992

    CAS  Google Scholar 

  32. Bose DS, Sudharshan M, Chavhan SW (2005) Arkivoc 3:228–236

    Google Scholar 

  33. Li N, Chen X-H, Song J, Luo S-W, Fan W, Gong L-Z (2009) J Am Chem Soc 131:15301–15310

    CAS  Google Scholar 

  34. Zhu C, Yang B, Zhao Y, Fu C, Tao L, Wei Y (2013) Polym Chem 4:5395–5400

    CAS  Google Scholar 

  35. Jenner G (2004) Tetrahedron Lett 45:6195–6198

    CAS  Google Scholar 

  36. Pramanik T, Wani TA, Singh A (2013) Orient J Chem 29:1209–1212

    CAS  Google Scholar 

  37. Khaleghi S, Heravi MM, Khosroshahi M, Kargar Behbahani F, Daroogheha Z (2008) Green Chem Lett Rev 1:133–139

    CAS  Google Scholar 

  38. Martínez J, Romero-Vega S, Abeja-Cruz R, Álvarez-Toledano C, Miranda R (2013) Int J Mol Sci 14:2903–2915

    Google Scholar 

  39. Kefayati H, Rad-Moghadam K, Zamani M, Hosseyni S (2010) Lett Org Chem 7:277–282

    CAS  Google Scholar 

  40. Svĕtlík J, Veizerová L (2011) Helv Chim Acta 94:199–205

    Google Scholar 

  41. Dzvinchuk IB, Makitruk TV, Lozinskii MO (2002) Chem Heterocycl Compd 38:1000–1007

    CAS  Google Scholar 

  42. Nadaraj V, Thamarai Selvi S, Abirami M, Daniel Thangadurai T (2014) Res J Recent Sci 3:370–374

    Google Scholar 

  43. Remennikov GY (1997) Chem Heterocycl Compd 33:1369–1381

    CAS  Google Scholar 

  44. Gong D, Zhang L, Yuan C (2003) Heteroat Chem 14:13–17

    CAS  Google Scholar 

  45. Vdovina SV, Mamedov VA (2008) Russ Chem Rev 77:1017

    CAS  Google Scholar 

  46. Essid I, Touil S (2013) Arkivoc 4:98–106

    Google Scholar 

  47. Nilsson BL, Overman LE (2006) J Org Chem 71:7706–7714

    CAS  Google Scholar 

  48. Alvim HGO, Lima TB, de Oliveira AL, de Oliveira HCB, Silva FM, Gozzo FC, Souza RY, da Silva WA, Neto BAD (2014) J Org Chem 79:3383–3397

    CAS  Google Scholar 

  49. Kundu SK, Majee A, Hajra A (2009) Indian J Chem 48:408–412

    Google Scholar 

  50. Dewan M, Kumar A, Saxena A, De A, Mozumdar S (2012) PLoS One 7:e43078

    CAS  Google Scholar 

  51. Bose DS, Fatima L, Mereyala HB (2003) J Org Chem 68:587–590

    CAS  Google Scholar 

  52. Dong F, Jun L, Xinli Z, Zhiwen Y, Zuliang L (2007) J Mol Catal A Chem 274:208–211

    CAS  Google Scholar 

  53. Alvim HGO, de Lima TB, de Oliveira HCB, Gozzo FC, de Macedo JL, Abdelnur PV, Silva WA, Neto BAD (2013) ACS Catal 3:1420–1430

    CAS  Google Scholar 

  54. Isambert N, Duque MdMS, Plaquevent J-C, Genisson Y, Rodriguez J, Constantieux T (2011) Chem Soc Rev 40:1347–1357

    CAS  Google Scholar 

  55. Tu S, Fang F, Zhu S, Li T, Zhang X, Zhuang Q (2004) Synlett 15:537–539

    Google Scholar 

  56. Yu Y, Liu D, Liu C, Jiang H, Luo G (2007) Prep Biochem Biotechnol 37:381–387

    CAS  Google Scholar 

  57. Salim SD, Akamanchi KG (2011) Catal Commun 12:1153–1156

    CAS  Google Scholar 

  58. Liberto NA, de Paiva Silva S, de Fátima Â, Fernandes SA (2013) Tetrahedron 69:8245–8249

    CAS  Google Scholar 

  59. Zhidovinova MS, Fedorova OV, Rusinov GL, Ovchinnikova IG (2003) Russ Chem Bull 52:2527–2528

    CAS  Google Scholar 

  60. Liu C-J, Wang J-D (2010) Molecules 15:2087–2095

    CAS  Google Scholar 

  61. Dallinger D, Kappe CO (2007) Nat Protoc 2:317–321

    CAS  Google Scholar 

  62. Harikrishnan PS, Rajesh SM, Perumal S, Almansour AI (2013) Tetrahedron Lett 54:1076–1079

    CAS  Google Scholar 

  63. Bose AK, Pednekar S, Ganguly SN, Chakraborty G, Manhas MS (2004) Tetrahedron Lett 45:8351–8353

    CAS  Google Scholar 

  64. Jayakumar S, Shabeer TK (2011) J Chem Pharm Res 3:1089–1096

    CAS  Google Scholar 

  65. Franzén RG (2000) J Comb Chem 2:195–214

    Google Scholar 

  66. Thompson LA (2000) Curr Opin Chem Biol 4:324–337

    CAS  Google Scholar 

  67. Xia M, Wang Y-G (2002) Tetrahedron Lett 43:7703–7705

    CAS  Google Scholar 

  68. Wang X, Quan Z, Wang F, Wang M, Zhang Z, Li Z (2006) Synth Commun 36:451–456

    CAS  Google Scholar 

  69. Lei M, Wu D-D, Wei H-G, Wang Y-G (2009) Synth Commun 39:475–483

    CAS  Google Scholar 

  70. Eynde JJV, Watté O (2003) Arkivoc 4:93–101

    Google Scholar 

  71. Wang Z-T, Wang S-C, Xu L-W (2005) Helv Chim Acta 88:986–989

    CAS  Google Scholar 

  72. Valverde MG, Dallinger D, Kappe CO (2001) Synlett 2001:0741–0744

    Google Scholar 

  73. Qin A, Lam JWY, Tang BZ (2010) Chem Soc Rev 39:2522–2544

    CAS  Google Scholar 

  74. Quemener D, Davis TP, Barner-Kowollik C, Stenzel MH (2006) Chem Commun 2006:5051–5053

    Google Scholar 

  75. Gauthier MA, Gibson MI, Klok H-A (2009) Angew Chem Int Ed 48:48–58

    CAS  Google Scholar 

  76. Kakuchi R (2014) Angew Chem Int Ed 53:46–48

    CAS  Google Scholar 

  77. Lowe AB (2014) Polym Chem 5:4820–4870

    CAS  Google Scholar 

  78. Billiet S, De Bruycker K, Driessen F, Goossens H, Van Speybroeck V, Winne JM, Prez FED (2014) Nat Chem 6:815–821

    CAS  Google Scholar 

  79. Tasdelen MA (2011) Polym Chem 2:2133–2145

    CAS  Google Scholar 

  80. Binder WH, Sachsenhofer R (2008) Macromol Rapid Commun 29:952–981

    CAS  Google Scholar 

  81. Gody G, Rossner C, Moraes J, Vana P, Maschmeyer T, Perrier S (2012) J Am Chem Soc 134:12596–12603

    CAS  Google Scholar 

  82. Hensarling RM, Rahane SB, LeBlanc AP, Sparks BJ, White EM, Locklin J, Patton DL (2011) Polym Chem 2:88–90

    CAS  Google Scholar 

  83. Kobayashi S, Makino A (2009) Chem Rev 109:5288–5353

    CAS  Google Scholar 

  84. Kreye O, Tóth T, Meier MAR (2011) J Am Chem Soc 133:1790–1792

    CAS  Google Scholar 

  85. Sehlinger A, Kreye O, Meier MAR (2013) Macromolecules 46:6031–6037

    CAS  Google Scholar 

  86. Solleder SC, Meier MAR (2014) Angew Chem Int Ed 53:711–714

    CAS  Google Scholar 

  87. Deng X-X, Cui Y, Du F-S, Li Z-C (2014) Polym Chem 5:3316–3320

    CAS  Google Scholar 

  88. Robotham C, Baker C, Cuevas B, Abboud K, Wright D (2003) Mol Diversity 6:237–244

    CAS  Google Scholar 

  89. Yang B, Zhao Y, Fu C, Zhu C, Zhang Y, Wang S, Wei Y, Tao L (2014) Polym Chem 5:2704–2708

    CAS  Google Scholar 

  90. Sehlinger A, Schneider R, Meier MAR (2014) Macromol Rapid Commun 35:1866–1871

    Google Scholar 

  91. McDonald CJ, Beaver RH (1979) Macromolecules 12:203–208

    CAS  Google Scholar 

  92. Ning X, Ishida H (1994) J Polym Sci Part A Polym Chem 32:1121–1129

    CAS  Google Scholar 

  93. Grimaldi S, Finet J-P, Le Moigne F, Zeghdaoui A, Tordo P, Benoit D, Fontanille M, Gnanou Y (2000) Macromolecules 33:1141–1147

    CAS  Google Scholar 

  94. Tai Q, Song L, Hu Y, Yuen RKK, Feng H, Tao Y (2012) Mater Chem Phys 134:163–169

    CAS  Google Scholar 

  95. Zhang Y, Zhao Y, Yang B, Zhu C, Wei Y, Tao L (2014) Polym Chem 5:1857–1862

    CAS  Google Scholar 

  96. Kakuchi R, Theato P (2014) ACS Macro Lett 3:329–332

    CAS  Google Scholar 

  97. Dharma Rao GB, Acharya BN, Kaushik MP (2013) Tetrahedron Lett 54:6644–6647

    CAS  Google Scholar 

  98. Novokshonov VV, Novokshonova IA, Nguyen HTT, Medvedeva AS (2011) Synth Commun 42:2346–2354

    Google Scholar 

  99. Salehi P, Dabiri M, Koohshari M, Movahed S, Bararjanian M (2011) Mol Diversity 15:833–837

    CAS  Google Scholar 

  100. Li M, De P, Gondi SR, Sumerlin BS (2008) J Polym Sci Part A Polym Chem 46:5093–5100

    CAS  Google Scholar 

  101. Koo SPS, Stamenović MM, Prasath RA, Inglis AJ, Prez FED, Barner-Kowollik C, Van Camp W, Junkers T (2010) J Polym Sci Part A Polym Chem 48:1699–1713

    CAS  Google Scholar 

  102. Hansell CF, Espeel P, Stamenovic MM, Barker IA, Dove AP, Prez FED, O’Reilly RK (2011) J Am Chem Soc 133:13828–13831

    CAS  Google Scholar 

  103. Levinger DC, Stevenson J-A, Wong L-L (1995) J Chem Soc Chem Commun 1995:2305–2306

    Google Scholar 

  104. Ponamarev MV, Longley MJ, Nguyen D, Kunkel TA, Copeland WC (2002) J Biol Chem 277:15225–15228

    CAS  Google Scholar 

  105. Barford D, Das AK, Egloff M-P (1998) Annu Rev Biophys Biomol Struct 27:133–164

    CAS  Google Scholar 

  106. Thomas M, Dadgar N, Aphale A, Harrell JM, Kunkel R, Pratt WB, Lieberman AP (2004) J Biol Chem 279:8389–8395

    CAS  Google Scholar 

  107. Garriga P, Liu X, Khorana HG (1996) Proc Natl Acad Sci USA 93:4560–4564

    CAS  Google Scholar 

  108. Reinicke S, Espeel P, Stamenović MM, Prez FED (2013) ACS Macro Lett 2:539–543

    CAS  Google Scholar 

  109. Lallana E, Tirelli N (2013) Macromol Chem Phys 214:143–158

    CAS  Google Scholar 

  110. Funhoff AM, van Nostrum CF, Lok MC, Fretz MM, Crommelin DJA, Hennink WE (2004) Bioconjug Chem 15:1212–1220

    CAS  Google Scholar 

  111. Ahmed M, Narain R (2013) Prog Polym Sci 38:767–790

    CAS  Google Scholar 

  112. Wu G, Sun W, Shen Z (2009) Chin J Polym Sci 27:293–296

    CAS  Google Scholar 

  113. Al-Nasassrah MA, Podczeck F, Newton JM (1998) Eur J Pharm Biopharm 46:31–38

    CAS  Google Scholar 

  114. Uchida K, Tamura A, Yajima H (2010) Biointerphases 5:17–21

    CAS  Google Scholar 

  115. Hoogenboom R, Thijs HML, Jochems MJHC, van Lankvelt BM, Fijten MWM, Schubert US (2008) Chem Commun 2008:5758–5760

    Google Scholar 

  116. Peter KW, Mary SN, Judy J, Joel BC (1997) Poly(ethylene glycol), vol 680. American Chemical Society, Washington, pp 45–57

    Google Scholar 

  117. Zhang Z, Kuijer R, Bulstra SK, Grijpma DW, Feijen J (2006) Biomaterials 27:1741–1748

    CAS  Google Scholar 

  118. Günay KA, Theato P, Klok H-A (2012) Functional polymers by post-polymerization modification. Wiley-VCH, Weinheim, pp 1–44

    Google Scholar 

  119. Mantovani G, Ladmiral V, Tao L, Haddleton DM (2005) Chem Commun 2005:2089–2091

    Google Scholar 

  120. Fu C, Tao L, Zhang Y, Li S, Wei Y (2012) Chem Commun 48:9062–9064

    CAS  Google Scholar 

  121. Wang S, Fu C, Zhang Y, Tao L, Li S, Wei Y (2012) ACS Macro Lett 1:1224–1227

    CAS  Google Scholar 

  122. Zhang Y, Fu C, Zhu C, Wang S, Tao L, Wei Y (2013) Polym Chem 4:466–469

    CAS  Google Scholar 

  123. Nakatani K, Terashima T, Sawamoto M (2009) J Am Chem Soc 131:13600–13601

    CAS  Google Scholar 

  124. Nakatani K, Ogura Y, Koda Y, Terashima T, Sawamoto M (2012) J Am Chem Soc 134:4373–4383

    CAS  Google Scholar 

  125. Ogura Y, Terashima T, Sawamoto M (2013) ACS Macro Lett 2:985–989

    CAS  Google Scholar 

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Tao, L., Zhu, C., Wei, Y., Zhao, Y. (2014). Biginelli Multicomponent Reactions in Polymer Science. In: Theato, P. (eds) Multi-Component and Sequential Reactions in Polymer Synthesis. Advances in Polymer Science, vol 269. Springer, Cham. https://doi.org/10.1007/12_2014_301

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