Abstract
Controlled microwave heating has found many important applications in the synthesis of heterocycles. Almost all kinds of heterocycles have been prepared (or their preparation attempted) with the aid of microwaves. Many examples of cyclocondensations, reactions where two or more functional groups combine with the loss of another small molecule (usually water), have been described. Moreover, microwave irradiation successfully induces cycloaddition reactions, especially in the cases where high temperatures are required. This review collects the most representative examples of the application of microwaves to these two kinds of transformations. Except for a few examples, all the reactions selected have been carried out under controlled microwave irradiation using dedicated instruments.
![](http://media.springernature.com/lw685/springer-static/image/chp%3A10.1007%2F7081_005/MediaObjects/ga_THC005.gif)
Preview
Unable to display preview. Download preview PDF.
Similar content being viewed by others
References
Kappe CO (2004) Angew Chem Int Ed 43:6250
Lew A, Krutznik PO, Hart ME, Chamberlin AR (2002) J Comb Chem 4:95
Kappe CO (2002) Curr Opin Chem Biol 6:314
Lidström P, Westman J, Lewis A (2002) Comb Chem High Throughput Screening 5:441
Blackwell HE (2003) Org Biomol Chem 1:1251
Baghurst DR, Mingos DMP (1992) J Chem Soc Chem Commun 674
Zhang X, Hayward DO, Mingos DMP (1999) J Chem Soc Chem Commun 975
Varma RS (1999) Green Chem 1:43
Tanaka K, Toda F (2000) Chem Rev 100:1025
Kuhnert N, Danks TN (2001) Green Chem 3:68
Clayden J, Greeves N, Warren S, Wothers P (2001) Organic Chemistry. Oxford University Press, Oxford
Joule JA, Mills K (2000) Heterocyclic chemistry, 4th edn. Blackwell Science, Oxford
Loupy A (ed) (2002) Microwaves in organic synthesis. Wiley, Weinheim
Hayes BL (2002) Microwave synthesis: chemistry at the speed of light. CEM Publishing, Matthews, NC
Lidström P, Tierny JP (2005) Blackwell Science, Oxford
For online resources of microwave-assisted synthesis, see: www.maos.net
Caddick S (1995) Tetrahedron 51:10403
Strauss CR (1999) Aust J Chem 52:83
de la Hoz A, Diaz-Ortis A, Moreno A, Langa F (2000) Eur J Org Chem 3659
Krstenansky JL, Cotterill I (2000) Curr Opin Drug Discovery Dev 3:454
Perreux L, Loupy A (2001) Tetrahedron 57:9199
Larhed M, Hallberg A (2001) Drug Discov Today 6:406
Lidstöm P, Tierny JP, Wathey B, Westman J (2001) Tetrahedron 57:9225
Bose AK, Manhas MS, Ganguly SN, Sharma AK, Banik BK (2002) Synthesis 1578
Xu Y, Guo Q-X (2004) Heterocycles 63:903
Bose AK, Manhas MS, Ghosh M, Shah M, Raju VS, Bari SS, Newaz SN, Banik BK, Chaudhary AG, Barakat KJ (1991) J Org Chem 56:6968
Linder MR, Podlech J (2001) Org Lett 3:1849
Liang Y, Jiao L, Zhang S, Xu J (2004) J Org Chem 70:334
Longchar M, Bora U, Boruah RC, Sandhu JS (2002) Synth Commun 32:3611
Danks TN (1999) Tetrahedron Lett 40:3957
Bharadwaj AR, Scheidt KA (2004) Org Lett 6:2465
Minetto G, Raveglia LF, Taddei M (2004) Org Lett 6:389
Alongi M, Minetto G, Taddei M (2005) Tetrahedron Lett 46:7069
Aydogan F, Demir AS (2005) Tetrahedron 61:3019
Werner S, Iyer PS (2005) Synlett 1405
Tejedor D, Gonzales-Crus D, Garcia-Tellado F, Marrero-Tellado JJ, Rodriguez ML (2004) J Am Chem Soc 126:8390
Kiryanov AA, Sampson P, Seed AJ (2001) J Org Chem 66:7925
Le Foulon F-X, Braud E, Fabis F, Lancelot J-C, Rault S (2003) Tetrahedron 10051
Rao HSP, Jothilingam S (2003) J Org Chem 68:5392
Sarshar S, Siev D, Mjalli MM (1996) Tetrahedron Lett 37:835
Reddy ACS, Rao PS, Venkataratnam RV (1997) Tetrahedron 53:5847
Bogdal D, Pielichowski J, Jaskot K (1997) Heterocycles 45:715
Usyatinsky AY, Khmelnistky YL (2000) Tetrahedron Lett 41:5031
Sparks RB, Combs AP (2004) Org Lett 6:2473
Coleman CM, MacElroy JMD, Gallagher JF, O'Shea DF (2002) J Comb Chem 4:87
Fresneda PM, Molina P, Sanz MA (2001) Synlett 218
Lee JC, Song I-G (2000) Tetrahedron Lett 41:5891
Moriarty RM, Vaid RK, Koser GF (1990) Synlett 365
Lee JC, Choi HJ, Lee YC (2003) Tetrahedron Lett 44:123
Martins MAP, Pereira CMP, Beck P, Machado P, Moura S, Teixeira MVM, Bonacorso HG, Zanatta N (2003) Tetrahedron Lett 44:6669
Giacomelli G, Porcheddu A, Salaris M, Taddei M (2003) Eur J Org Chem 537
Arrieta A, Carrillo JR, Cossio FP, Diaz-Ortiz A, Gomez-Escalonilla MJ, de la Hoz A, Langa F, Moreno A (1998) Tetrahedron 54:13167
Bentiss F, Lagrenee M, Barbry D (2000) Tetrahedron Lett 41:1539
Katritzky AR, Singh SK (2002) J Org Chem 67:9077
Savin KA, Robertson M, Gernet D, Green S, Hembre EJ, Bishop J (2003) Mol Divers 7:171
Khanetsky B, Dallinger D, Kappe CO (2004) J Comb Chem 6:884
Kaval N, Ermolat'ev D, Appukkuttan P, Dehaen W, Kappe CO, Van der Eyken E (2005) J Comb Chem 7:490
Ermolatev D, Dehaen W, Van der Eyken E (2004) QSAR Comb Sci 23:915
Habermann J, Ley SV, Scott JS (1998) J Chem Soc Chem Commun 3127
Brain CT, Paul JM, Loong Y, Oakley PJ (1999) Tetrahedron Lett 40:3275
Bentiss F, Lagrenee M, Barbry D (2001) Synth Commun 31:935
Natero R, Koltun DO, Zablocki JA (2004) Synth Commun 34:2523
Alterman M, Hallberg A (2000) J Org Chem 65:7984
Bentabed G, Derdour A, Banhaoua H (2003) Synth Commun 33:1861
Liao L, Villemin D (2000) J Chem Res (S) 179
Liu SHaller MA, Ma H, Dalton LR, Jang S-H, Jen AK-Y (2003) Adv Mater 15:603
Lamberto M, Corbett DF, Kilburn JD (2003) Tetrahedron Lett 44:1347
Huisgen R (1963) Angew Chem Int Ed Engl 2:565
Diaz-Ortis A, de la Hoz A, Herrero MA, Prieto P, Sanchez-Migallon A, Cossio FP, Arrieta A, Vivanco S, Foces-Foces C (2003) Mol Divers 7:175
Pospisil J, Potacek M (2004) Eur J Org Chem 710
Zhang W, Lu Y, Gelb S (2005) Org Lett 7:2269
Bashiardes G, Safir I, Mohamed AS, Barbot F, Laduranty J (2003) Org Lett 5:4915
Aly MF, Younes MI, Metwally SAM (1994) Tetrahedron 50:3159
Wilson NS, Sarko CR, Roth GP (2001) Tetrahedron Lett 42:8939
Langa F, de la Cruz P, de la Hoz A, Espildora E, Cossio FP, Lecea B (2000) J Org Chem 65:2499
de la Cruz P, Espildora E, Garcia JJ, de la Hoz A, Langa F, Martin N, Sanchez L (1999) Tetrahedron Lett 40:4889
Pospisil J, Potacek M (2004) Heterocycles 63:1165
Merriman GH, Ma L, Shum P, McGarry D, Volz F, Sabol JS, Gross A, Zhao Z, Rampe D, Wang L, Wirtz-Brugger F, Harris BA, Macdonald D (2005) Bioorg Med Chem Lett 15:435
Meddad N, Rahmouni M, Derdour A, Bazureau JP, Hamelin J (2001) Synthesis 581
Cox CD, Breslin MJ, Mariano BJ (2004) Tetrahedron Lett 45:1489
Garcia-Tellado F, Loupy A, Petit A, Marrero-Terrero AL (2003) Eur J Org Chem 4387
Katritzky AR, Cai C, Suzuki K, Singh SK (2004) J Org Chem 69:811
Crosignani S, Young AC, Linclau B (2004) Tetrahedron Lett 45:9611
Diwischek F, Heller E, Holzgrabe U (2003) Monatsh Chemie 134:1105
Kuhnert N, Danks TN (2001) Green Chem 3:68
Trost BM, Dogra K, Franzini M (2004) J Am Chem Soc 126:1944
Raunak KV, Mukherjee S, Poonam PAK, Olsen CE, Schaffer SJC, Sharma SK, Watterson AC, Errington W, Parmar VS (2005) Tetrahedron 61:5687
Gududuru V, Nguyen V, Dalton JT, Miller DD (2004) Synlett 2357
Desasi B, Danks TN, Wagner G (2003) Perkin Trans I 2544
Charmier MAJ, Yu V, Kukuskin SJ, Pombeiro AJL (2003) Perkin Trans I 2540
Gong YD, Kurth MJ (1998) Tetrahedron Lett 39:3379
Gong YD, Sohn HY, Kurth MJ (1998) J Org Chem 63:4854
Perio B, Dozias MJ, Jacquault P, Hamelin J (1997) Tetrahedron Lett 38:7867
Ferrett RR, Hyde MJ, Lahti KA, Friebe TL (2003) Tetrahedron Lett 44:2573
Perio B, Dozias MJ, Hamelin J (1998) Org Proc Res & Dev 2:428
Kim YJ, Varma RS (2004) Tetrahedron Lett 45:7205
Penieres G, Garcia O, Franco K, Hernandez O, Alvarez C (1996) Hetrocycl Commun 2:359
Cotterill IC, Ya A, Usyatinsky AY, Arnold JM, Clark DS, Dordick JS, Michels PC, Khmelnitsky YL (1998) Tetrahedron Lett 39:1117
Öhberg L, Westman J (2001) Synlett 1296
Tu S, Miao C, Fang F, Youjian F, Li T, Zhuang Q, Zhang X, Zhu S, Shi D (2004) Bioorg Med Chem Lett 14:1533
Khadilkar BM, Madyar VR (2001) Org Proc Res Dev 5:452
Bagley MC, Lunn R, **ong X (2002) Tetrahedron Lett 43:8331
Bagley MC, **ong X (2004) Org Lett 6:3401
Bagley MC, Hughes DD, Taylor PH (2003) Synlett 259
Lampariello LR, Minetto G, Taddei M (2005) Synlett
Peng Y, Song G (2004) Tetrahedron Lett 45:5313
Zhao Z, Leister WH, Strauss KA, Wisnoski DD, Lindsley CW (2003) Tetrahedron Lett 44:1123
Sandin H, Swanstein ML, Wellner E (2004) J Org Chem 69:1571
Rodriguez H, Suarez M, Perez R, Petit A, Loupy A (2004) Tetrahedron Lett 44:3709
Giannotti M, Martelli G, Mendozza M, Panunzio M, Campana E (2000) Synth Commun 30:1725
Panunzio M, Lentini MA, Campana E, Martelli G, Tamanini E, Vicennati P (2004) Synth Commun 34:345
Bose AK, Manhas MS, Ghosh M, Raju VS, Tabei K, Urbanczylk-Lipkowska Z (1990) Heterocycles 30:741
Bose AK (1973) Org Synth Coll Vol V:973
Borah NH, Boruah RC, Sandhu JS (1998) J Chem Res (S) 272
Peng Y, Song G, Qian X (2001) Synth Commun 31:1927
Mortoni A, Martinelli M, Piarulli U, Regalia N, Gagliardi S (2004) Tetrahedron Lett 45:6623
Chandrasekhar S, Takhi M, Uma G (1997) Tetrahedron Lett 38:8089
Vidal T, Petit A, Luopy A, Gedye RN (2000) Tetrahedron 56:5473
Lipinska T (2002) Tetrahedron Lett 43:9565
Bogdal D, Warzala M (2000) Tetrahedron 56:8769
Kabalka GW, Wang L, Pagni RM (2001) Tetrahedron Lett 42:6049
Allen D, Callaghan O, Cordier FL, Dobson DR, Harris JR, Hotten TM, Owton WM, Rathmell RE, Wood VA (2004) Tetrahedron Lett 45:9645
Boot JR, Brace G, Delatour CL, Dezutter N, Fairhurst J, Findlay J, Gallagher PT, Hoes I, Mahadevan S, Mitchell SN, Rathmell RE, Richards SJ, Simmonds RG, Wallace L, Whatton MA (2004) Bioorg Med Chem Lett 14:5395
Ferro S, Rao A, Zappalà M, Chimirri A, Barreca ML, Witvrouw M, Debyser Z, Monteforte P (2004) Heterocycles 63:2727
Pottorf RS, Chadha NK, Katkevics M, Ozola V, Suna E, Ghane H, Regberg T, Player MK (2003) Tetrahedron Lett 44:175
Garnier E, Blanchard S, Rodriguez I, Jarry C, Leger JM, Caubère P, Guillaumet G (2003) Synthesis 2033
Diaz-Ortiz A, Carrillo JR, Gomez-Escalonilla MJ, de la Hoz A, Moreno A, Prieto P (1998) Synlett 1069
Diaz-Ortiz A, Carrillo JR, Cossio FP, Gomez-Escalonilla MJ, de la Hoz A, Moreno A, Prieto P (2000) Tetrahedron 56:1569
Diaz-Ortiz A, de la Hoz A, Prieto P, Carrillo, JR Moreno A, Neunhoeffer H (2001) Synlett 236
Pinto DCGA, Silva AMS, Almeida LMPM, Carrillo JR, Diaz-Ortiz A, de la Hoz A (2003) Synlett 1415
Mance AD, Jakopcic K (2005) Mol Divers 9:229
Shao B (2005) Tetrahedron Lett 46:3423
Dymock B, Barril X, Beswick M, Collier A, Davies N, Drysdale M, Fink A, Fromont C, Hubbard RE, Massey A, Surgenor A, Wright L (2004) Bioorg Med Chem Lett 14:325
Devi I, Borah HN, Bhuyan PJ (2004) Tetrahedron Lett 45:2405
Gohain M, Prajapati D, Gogoi BJ, Sandhu JS (2004) Synlett 1179
Theoclitou ME, Robinson LA (2002) Tetrahedron Lett 43:3907
Ranu BC, Hajra A, Jana U (2000) Tetrahedron Lett 41:531
Song SJ, Cho SJ, Park DK, Kwon TW, Jenekhe SA (2003) Tetrahedron Lett 44:255
Lange JHM, Verveer PC, Osnabrug SJM, Visser GM (2001) Tetrahedron Lett 42:1367
Sanchez-Sancho F, Mann E, Herradon B (2000) Synlett 509
Dai WM, Wang X, Ma C (2005) Tetrahedron 61:6879
Zhao Z, Wisnoski DD, Wolkenberg SE, Leister WH, Wang Y, Lindsley CW (2004) Tetrahedron Lett 45:4873
von Niementowski S (1895) J Prakt Chem 51:564
Alexandre FR, Berecibar A, Besson T (2002) Tetrahedron Lett 43:3911
Sethna S, Phadka R (1953) Org React 7:1
Frere S, Thiery V, Besson T (2001) Tetrahedron Lett 42:2791
de la Hoz A, Moreno A, Vasquez E (1999) Synlett 608
Seijas JA, Vazquez-Tato MP, Carballido-Roboredo R (2005) J Org Chem 70:2855
Cox ED, Cook JM (1995) Chem Rev 95:1797
Srinivasan N, Ganesan A (2003) Chem Commun 916
Yen YH, Chu YH (2004) Tetrahedron Lett 45:8137
Campiglia P, Gomez-Monterrey I, Lama T, Novellino E, Grieco P (2004) Mol Divers 8:427
Kuo FM, Tseng MC, Yen YH, Chu YH (2004) Tetrahedron 60:12075
Masengeau C, Yous S, Peres B, Lesieur D, Besson T (2005) Tetrahedron Lett 46:2465
Traynelis VJ, Hergenrother WL (1964) J Org Chem 29:221
Paul S, Gupta M, Gupta R, Loupy A (2001) Tetrahedron Lett 42:3827
Abbiati G, Arcadi A, Bellinazzi A, Beccali E, Rossi E, Zanzola S (2005) J Org Chem 70:4088
Stadler A, Pichler S, Horeis G, Kappe CO (2002) Tetrahedron 58:3177
Fresneda PM, Molina P, Delgado S (2001) Tetrahedron 57:6197
Perzyna A, Houssin R, Barbry D, Henichart JP (2002) Synlett 2077
Nemes P, Vincze Z, Balazs B, Toth G, Scheiber P (2003) Synlett 250
Santagada V, Perissutti E, Fiorino F, Vivenzio B, Caliendo G (2001) Tetrahedron Lett 42:2397
Holzgrabe U, Heller E (2003) Tetrahedron 59:781
Grieco P, Campiglia P, Gomez-Monterrey I, Lama T, Novellino E (2003) Synlett 14:2216
Srimurugan S, Viswanathan B, Varadarajan TK, Varghese B (2005) Tetrahedron Lett 46:3151
Author information
Authors and Affiliations
Corresponding author
Editor information
Rights and permissions
About this chapter
Cite this chapter
Rodriquez, M., Taddei, M. Synthesis of Heterocycles via Microwave-Assisted Cycloadditions and Cyclocondensations. In: Van der Eycken, E., Kappe, C.O. (eds) Microwave-Assisted Synthesis of Heterocycles. Topics in Heterocyclic Chemistry, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_005
Download citation
DOI: https://doi.org/10.1007/7081_005
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-30983-3
Online ISBN: 978-3-540-34481-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)