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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Tron GC, Minassi A, Appendino G (2011) Eur J Org Chem 2011:5541–5550
Aron ZD, Overman LE (2004) Chem Commun 2004:253–265
Kappe CO (2000) Acc Chem Res 33:879–888
Dharma Rao GB, Anjaneyulu B, Kaushik MP (2014) Tetrahedron Lett 55:19–22
Oliverio M, Costanzo P, Nardi M, Rivalta I, Procopio A (2014) ACS Sustainable Chem Eng 2:1228–1233
Kappe CO (2000) Eur J Med Chem 35:1043–1052
Sandhu JS (2012) Arkivoc 1:66–133
Sabitha G, Kiran Kumar Reddy GS, Reddy S, Yadav JS (2003) Synlett 2003:0858–0860
Bose AK, Manhas MS, Pednekar S, Ganguly SN, Dang H, He W, Mandadi A (2005) Tetrahedron Lett 46:1901–1903
Panda SS, Khanna P, Khanna L (2012) Curr Org Chem 16:507–520
Warekar PP, Kolekar GB, Deshmukh MB, Anbhule PV (2014) Synth Commun 44:3594–3601
Kappe CO (2003) QSAR Comb Sci 22:630–645
Stadler A, Kappe CO (2001) J Comb Chem 3:624–630
Sabitha G, Reddy GS, Reddy KB, Yadav JS (2003) Tetrahedron Lett 44:6497–6499
Khanetskyy B, Dallinger D, Kappe CO (2004) J Comb Chem 6:884–892
Wipf P, Cunningham A (1995) Tetrahedron Lett 36:7819–7822
Cushman M, Nagarathnam D, Burg DL, Geahlen RL (1991) J Med Chem 34:798–806
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
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
Jadhav VB, Holla HV, Tekale SU, Pawar RP (2012) Der Chem Sin 3:1213–1228
Grover GJ, Dzwonczyk S, McMullen DM, Normandin DE, Parham CS, Sleph PG, Moreland S (1995) J Cardiovasc Pharmacol 26:289–294
Chikhale RV, Bhole RP, Khedekar PB, Bhusari KP (2009) Eur J Med Chem 44:3645–3653
Marvaniya HM, Parikh PK, Sen DJ (2011) J Appl Pharm Sci 1:109–113
Lewis RW, Mabry J, Polisar JG, Eagen KP, Ganem B, Hess GP (2010) Biochemistry 49:4841–4851
Trivedi AR, Bhuva VR, Dholariya BH, Dodiya DK, Kataria VB, Shah VH (2010) Bioorg Med Chem Lett 20:6100–6102
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
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
Deshmukh MB, Salunkhe SM, Patil DR, Anbhule PV (2009) Eur J Med Chem 44:2651–2654
Chitra S, Devanathan D, Pandiarajan K (2010) Eur J Med Chem 45:367–371
Tawfik HA, Bassyouni F, Gamal-Eldeen AM, Abo-Zeid MA, El-Hamouly WS (2009) Pharmacol Rep 61:1153–1162
Agbaje OC, Fadeyi OO, Fadeyi SA, Myles LE, Okoro CO (2011) Bioorg Med Chem Lett 21:989–992
Bose DS, Sudharshan M, Chavhan SW (2005) Arkivoc 3:228–236
Li N, Chen X-H, Song J, Luo S-W, Fan W, Gong L-Z (2009) J Am Chem Soc 131:15301–15310
Zhu C, Yang B, Zhao Y, Fu C, Tao L, Wei Y (2013) Polym Chem 4:5395–5400
Jenner G (2004) Tetrahedron Lett 45:6195–6198
Pramanik T, Wani TA, Singh A (2013) Orient J Chem 29:1209–1212
Khaleghi S, Heravi MM, Khosroshahi M, Kargar Behbahani F, Daroogheha Z (2008) Green Chem Lett Rev 1:133–139
Martínez J, Romero-Vega S, Abeja-Cruz R, Álvarez-Toledano C, Miranda R (2013) Int J Mol Sci 14:2903–2915
Kefayati H, Rad-Moghadam K, Zamani M, Hosseyni S (2010) Lett Org Chem 7:277–282
Svĕtlík J, Veizerová L (2011) Helv Chim Acta 94:199–205
Dzvinchuk IB, Makitruk TV, Lozinskii MO (2002) Chem Heterocycl Compd 38:1000–1007
Nadaraj V, Thamarai Selvi S, Abirami M, Daniel Thangadurai T (2014) Res J Recent Sci 3:370–374
Remennikov GY (1997) Chem Heterocycl Compd 33:1369–1381
Gong D, Zhang L, Yuan C (2003) Heteroat Chem 14:13–17
Vdovina SV, Mamedov VA (2008) Russ Chem Rev 77:1017
Essid I, Touil S (2013) Arkivoc 4:98–106
Nilsson BL, Overman LE (2006) J Org Chem 71:7706–7714
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
Kundu SK, Majee A, Hajra A (2009) Indian J Chem 48:408–412
Dewan M, Kumar A, Saxena A, De A, Mozumdar S (2012) PLoS One 7:e43078
Bose DS, Fatima L, Mereyala HB (2003) J Org Chem 68:587–590
Dong F, Jun L, Xinli Z, Zhiwen Y, Zuliang L (2007) J Mol Catal A Chem 274:208–211
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
Isambert N, Duque MdMS, Plaquevent J-C, Genisson Y, Rodriguez J, Constantieux T (2011) Chem Soc Rev 40:1347–1357
Tu S, Fang F, Zhu S, Li T, Zhang X, Zhuang Q (2004) Synlett 15:537–539
Yu Y, Liu D, Liu C, Jiang H, Luo G (2007) Prep Biochem Biotechnol 37:381–387
Salim SD, Akamanchi KG (2011) Catal Commun 12:1153–1156
Liberto NA, de Paiva Silva S, de Fátima Â, Fernandes SA (2013) Tetrahedron 69:8245–8249
Zhidovinova MS, Fedorova OV, Rusinov GL, Ovchinnikova IG (2003) Russ Chem Bull 52:2527–2528
Liu C-J, Wang J-D (2010) Molecules 15:2087–2095
Dallinger D, Kappe CO (2007) Nat Protoc 2:317–321
Harikrishnan PS, Rajesh SM, Perumal S, Almansour AI (2013) Tetrahedron Lett 54:1076–1079
Bose AK, Pednekar S, Ganguly SN, Chakraborty G, Manhas MS (2004) Tetrahedron Lett 45:8351–8353
Jayakumar S, Shabeer TK (2011) J Chem Pharm Res 3:1089–1096
Franzén RG (2000) J Comb Chem 2:195–214
Thompson LA (2000) Curr Opin Chem Biol 4:324–337
Xia M, Wang Y-G (2002) Tetrahedron Lett 43:7703–7705
Wang X, Quan Z, Wang F, Wang M, Zhang Z, Li Z (2006) Synth Commun 36:451–456
Lei M, Wu D-D, Wei H-G, Wang Y-G (2009) Synth Commun 39:475–483
Eynde JJV, Watté O (2003) Arkivoc 4:93–101
Wang Z-T, Wang S-C, Xu L-W (2005) Helv Chim Acta 88:986–989
Valverde MG, Dallinger D, Kappe CO (2001) Synlett 2001:0741–0744
Qin A, Lam JWY, Tang BZ (2010) Chem Soc Rev 39:2522–2544
Quemener D, Davis TP, Barner-Kowollik C, Stenzel MH (2006) Chem Commun 2006:5051–5053
Gauthier MA, Gibson MI, Klok H-A (2009) Angew Chem Int Ed 48:48–58
Kakuchi R (2014) Angew Chem Int Ed 53:46–48
Lowe AB (2014) Polym Chem 5:4820–4870
Billiet S, De Bruycker K, Driessen F, Goossens H, Van Speybroeck V, Winne JM, Prez FED (2014) Nat Chem 6:815–821
Tasdelen MA (2011) Polym Chem 2:2133–2145
Binder WH, Sachsenhofer R (2008) Macromol Rapid Commun 29:952–981
Gody G, Rossner C, Moraes J, Vana P, Maschmeyer T, Perrier S (2012) J Am Chem Soc 134:12596–12603
Hensarling RM, Rahane SB, LeBlanc AP, Sparks BJ, White EM, Locklin J, Patton DL (2011) Polym Chem 2:88–90
Kobayashi S, Makino A (2009) Chem Rev 109:5288–5353
Kreye O, Tóth T, Meier MAR (2011) J Am Chem Soc 133:1790–1792
Sehlinger A, Kreye O, Meier MAR (2013) Macromolecules 46:6031–6037
Solleder SC, Meier MAR (2014) Angew Chem Int Ed 53:711–714
Deng X-X, Cui Y, Du F-S, Li Z-C (2014) Polym Chem 5:3316–3320
Robotham C, Baker C, Cuevas B, Abboud K, Wright D (2003) Mol Diversity 6:237–244
Yang B, Zhao Y, Fu C, Zhu C, Zhang Y, Wang S, Wei Y, Tao L (2014) Polym Chem 5:2704–2708
Sehlinger A, Schneider R, Meier MAR (2014) Macromol Rapid Commun 35:1866–1871
McDonald CJ, Beaver RH (1979) Macromolecules 12:203–208
Ning X, Ishida H (1994) J Polym Sci Part A Polym Chem 32:1121–1129
Grimaldi S, Finet J-P, Le Moigne F, Zeghdaoui A, Tordo P, Benoit D, Fontanille M, Gnanou Y (2000) Macromolecules 33:1141–1147
Tai Q, Song L, Hu Y, Yuen RKK, Feng H, Tao Y (2012) Mater Chem Phys 134:163–169
Zhang Y, Zhao Y, Yang B, Zhu C, Wei Y, Tao L (2014) Polym Chem 5:1857–1862
Kakuchi R, Theato P (2014) ACS Macro Lett 3:329–332
Dharma Rao GB, Acharya BN, Kaushik MP (2013) Tetrahedron Lett 54:6644–6647
Novokshonov VV, Novokshonova IA, Nguyen HTT, Medvedeva AS (2011) Synth Commun 42:2346–2354
Salehi P, Dabiri M, Koohshari M, Movahed S, Bararjanian M (2011) Mol Diversity 15:833–837
Li M, De P, Gondi SR, Sumerlin BS (2008) J Polym Sci Part A Polym Chem 46:5093–5100
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
Hansell CF, Espeel P, Stamenovic MM, Barker IA, Dove AP, Prez FED, O’Reilly RK (2011) J Am Chem Soc 133:13828–13831
Levinger DC, Stevenson J-A, Wong L-L (1995) J Chem Soc Chem Commun 1995:2305–2306
Ponamarev MV, Longley MJ, Nguyen D, Kunkel TA, Copeland WC (2002) J Biol Chem 277:15225–15228
Barford D, Das AK, Egloff M-P (1998) Annu Rev Biophys Biomol Struct 27:133–164
Thomas M, Dadgar N, Aphale A, Harrell JM, Kunkel R, Pratt WB, Lieberman AP (2004) J Biol Chem 279:8389–8395
Garriga P, Liu X, Khorana HG (1996) Proc Natl Acad Sci USA 93:4560–4564
Reinicke S, Espeel P, Stamenović MM, Prez FED (2013) ACS Macro Lett 2:539–543
Lallana E, Tirelli N (2013) Macromol Chem Phys 214:143–158
Funhoff AM, van Nostrum CF, Lok MC, Fretz MM, Crommelin DJA, Hennink WE (2004) Bioconjug Chem 15:1212–1220
Ahmed M, Narain R (2013) Prog Polym Sci 38:767–790
Wu G, Sun W, Shen Z (2009) Chin J Polym Sci 27:293–296
Al-Nasassrah MA, Podczeck F, Newton JM (1998) Eur J Pharm Biopharm 46:31–38
Uchida K, Tamura A, Yajima H (2010) Biointerphases 5:17–21
Hoogenboom R, Thijs HML, Jochems MJHC, van Lankvelt BM, Fijten MWM, Schubert US (2008) Chem Commun 2008:5758–5760
Peter KW, Mary SN, Judy J, Joel BC (1997) Poly(ethylene glycol), vol 680. American Chemical Society, Washington, pp 45–57
Zhang Z, Kuijer R, Bulstra SK, Grijpma DW, Feijen J (2006) Biomaterials 27:1741–1748
Günay KA, Theato P, Klok H-A (2012) Functional polymers by post-polymerization modification. Wiley-VCH, Weinheim, pp 1–44
Mantovani G, Ladmiral V, Tao L, Haddleton DM (2005) Chem Commun 2005:2089–2091
Fu C, Tao L, Zhang Y, Li S, Wei Y (2012) Chem Commun 48:9062–9064
Wang S, Fu C, Zhang Y, Tao L, Li S, Wei Y (2012) ACS Macro Lett 1:1224–1227
Zhang Y, Fu C, Zhu C, Wang S, Tao L, Wei Y (2013) Polym Chem 4:466–469
Nakatani K, Terashima T, Sawamoto M (2009) J Am Chem Soc 131:13600–13601
Nakatani K, Ogura Y, Koda Y, Terashima T, Sawamoto M (2012) J Am Chem Soc 134:4373–4383
Ogura Y, Terashima T, Sawamoto M (2013) ACS Macro Lett 2:985–989
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer International Publishing Switzerland
About this chapter
Cite this chapter
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
Download citation
DOI: https://doi.org/10.1007/12_2014_301
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-20719-3
Online ISBN: 978-3-319-20720-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)