Abstract
Recent developments in the microwave-assisted synthesis of heterocycles are surveyed with the focus on diversity-oriented multi-component and multi-step one-pot procedures. Both solution- and solid-phase as well as polymer-supported methodologies for the preparation of libraries of heterocycles are reviewed. Advantages of microwave dielectric heating are highlighted by comparison with conventional thermal conditions.
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Abbreviations
- BEMP:
-
2-tert-butylimino-2-dimethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine
- DBU:
-
1,8-diazabicyclo[5.4.0]undec-7-ene
- DHP:
-
dihydropyridine
- DIEA:
-
diisopropylethylamine
- DMAP:
-
4-(dimethylamino)pyridine
- DMF:
-
N,N-dimethylformamide
- DMF–DMA:
-
N,N-dimethylformamide dimethyl acetal
- HBTU:
-
O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate
- HMDS:
-
hexamethyldisilazane
- IL:
-
ionic liquids
- MCR:
-
multi-component reaction
- MW:
-
microwaves
- NBS:
-
N-bromosuccinimide
- NMP:
-
N-methyl-2-pyrrolidinone
- PEG:
-
poly(ethylene glycol)
- PPTS:
-
pyridinium p-toluenesulfonate
- PS:
-
polymer supported
- RCM:
-
ring-closing metathesis
- SPE:
-
solid-phase extraction
- SPOS:
-
solid-phase organic synthesis
- TFA:
-
trifluoroacetic acid
- THF:
-
tetrahydrofuran
- TMS:
-
trimethylsilyl
- Ts:
-
tosyl (p-toluenesulfonyl)
References
Kappe CO, Dallinger D (2006) Nature Rev: Drug Disc 5:51
Tietze LF (1996) Chem Rev 96:115
Mingos DMP, Baghurst DR (1991) Chem Soc Rev 20:1
Bagnell L, Bliese M, Cablewski T, Strauss CR, Tsanaktsidis J (1997) Aust J Chem 50:921
Bagnell L, Cablewski T, Strauss CR, Trainor RW (1996) J Org Chem 61:7355
Hamelin J, Bazureau J-P, Texier-Boullet F (2002) Microwaves in Heterocyclic Chemistry. In: Loupy A (ed) Microwaves in Organic Synthesis. Wiley, Weinheim, p 253
Besson T, Brain CT (2004) Heterocyclic Chemistry Using Microwave-Assisted Approaches. In: Lidström P, Tierney JP (eds) Microwave-Assisted Organic Synthesis. Blackwell, Oxford, p 44
Xu Y, Guo Q-X (2004) Heterocycles 63:903
Kappe CO, Stadler A (2005) Microwaves in Organic and Medicinal Chemistry. Wiley, Weinheim
Molteni V, Ellis DA (2005) Curr Org Synth 2:333
Westman J (2004) Speed and Efficiency in the Production of Diverse Structures: Microwave-Assisted Multicomponent Reactions. In: Lidström P, Tierney JP (eds) Microwave-Assisted Organic Synthesis. Blackwell, Oxford, p 102
Ju Y, Varma RS (2005) Org Lett 7:2409
Ju Y, Varma RS (2006) J Org Chem 71:135
Mayo KG, Nearhoof EH, Kiddle JJ (2002) Org Lett 4:1567
Grigg R, Martin W, Morrisa J, Sridharana V (2003) Tetrahedron Lett 44:4899
Balan D, Adolfsson H (2004) Tetrahedron Lett 45:3089
Declerck V, Ribière P, Martinez J, Lamaty F (2004) J Org Chem 69:8372
Perreux L, Loupy A (2002) Nonthermal Effects of Microwaves in Organic Synthesis. In: Loupy A (ed) Microwaves in Organic Synthesis. Wiley, Weinheim, p 61
Kuhnert N (2002) Angew Chem Int Ed 41:1863
Strauss CR (2002) Angew Chem Int Ed 41:3589
Garbacia S, Desai B, Lavastre O, Kappe CO (2003) J Org Chem 68:9136
Minetto G, Raveglia LF, Taddei M (2004) Org Lett 6:389
Rao HSP, Jothilingam S, Scheeren HW (2004) Tetrahedron 60:1625
Tejedor D, González-Cruz D, Garcia-Tellado F, Marrero-Tellado JJ, Rodriguez ML (2004) J Am Chem Soc 126:8390
Bashiardes G, Safir I, Mohamed AS, Barbot F, Laduranty J (2003) Org Lett 5:4915
Perreux L, Loupy A (2001) Tetrahedron 57:9199
Joule JA, Mills K (2000) Heterocyclic Chemistry. Blackwell Science, Oxford
Siu J, Baxendale IR, Ley SV (2004) Org Biomol Chem 2:160
Lipińska TM (2004) Tetrahedron Lett 45:8831
Lipińska TM, Czarnocki SJ (2006) Org Lett 8:367
Lachance N, April M, Joly M-A (2005) Synthesis 2571
Poondra RR, Turner NJ (2005) Org Lett 7:863
Akamatsu H, Fukase K, Kusumoto S (2004) Synlett, p 1049
Bora U, Saikia A, Boruah RC (2003) Org Lett 5:435
Barchin BM, Cuadro AM, Alvarez-Builla J (2002) Synlett, p 343
Appukkuttan P, Van der Eycken E, Dehaen W (2005) Synlett, p 127
Bouchard J, Wakim S, Leclerc M (2004) J Org Chem 69:5705
Hoener APF, Henkel B, Gauvin J-C (2003) Synlett, p 63
Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao Z, Lindsley CW (2004) Org Lett 6:1453
Xu Y, Wan L-F, Salehi H, Deng W, Guo Q-X (2004) Heterocycles 63:1613
Sparks RB, Combs AP (2004) Org Lett 6:2473
Balalaie S, Hashemi MM, Akhbari M (2003) Tetrahedron Lett 44:1709
Coleman CM, MacElroy JMD, Gallagher JF, O'Shea DF (2002) J Comb Chem 4:87
Durand-Reville T, Gobbi LB, Gray BL, Ley SV, Scott JS (2002) Org Lett 4:3847
De Luca L, Giacomelli G, Porcheddu A (2005) J Comb Chem 7:905
Henkel B (2004) Tetrahedron Lett 45:2219
Kim YJ, Varma RS (2004) Tetrahedron Lett 45:7205
Boufatah N, Gellis A, Maldonado J, Vanelle P (2004) Tetrahedron 60:9131
VanVliet DS, Gillespie P, Scicinski JJ (2005) Tetrahedron Lett 46:6741
Perumal S, Mariappan S, Selvaraj S (2004) ARKIVOC viii, p 46
Brain CT, Steer JT (2003) J Org Chem 68:6814
Ireland SM, Tye H, Whittaker M (2003) Tetrahedron Lett 44:4369
Schwerkoske J, Masquelin T, Perun T, Hulme C (2005) Tetrahedron Lett 46:8355
Lu Y, Zhang W (2004) QSAR Combi Sci 23:827
Bendale PM, Sun C-M (2002) J Comb Chem 4:359
Lin M-J, Sun C-M (2004) Synlett, p 663
Su Y-S, Lin M-J, Sun M-C (2004) Tetrahedron Lett 46:177
Su Y-S, Sun M-C (2005) Synlett, p 1243
Lee M-J, Sun C-M (2004) Tetrahedron Lett 45:437
Lin M-J, Sun C-M (2003) Tetrahedron Lett 44:8739
Yeh W-B, Lin M-J, Lee M-J, Sun C-M (2003) Molecular Diversity 7:185
Paul S, Gupta M, Gupta R, Loupy A (2002) Synthesis, p 75
Muccioli GG, Poupaert JH, Wouters J, Norberg B, Poppitz W, Scriba GKE, Lambert DM (2003) Tetrahedron 59:1301
Molteni V, Hamilton MM, Mao L, Crane CM, Termin AP, Wilson DM (2002) Synthesis, p 1669
Westman J, Lundin R, Stalberg J, Ostbye M, Franzen A, Hurynowicz A (2002) Comb Chem High Throughput Screen 5:565
Giacomelli G, Porcheddu A, Salaris M, Taddei M (2003) Eur J Org Chem, p 537
Westman J, Lundin R (2003) Synthesis, p 1025
De Luca L, Giacomelli G, Porcheddu A, Salaris M, Taddei M (2003) J Comb Chem 5:465
Giacomelli G, De Luca L, Porcheddu A (2003) Tetrahedron 59:5437
Chiacchio U, Rescifina A, Saita MG, Iannazzo D, Romeo G, Mates JA, Tejero T, Merino P (2005) J Org Chem 70:8991
Vasquez TE, Nixey T, Chenera B, Gore V, Bartberger MD, Sun Y, Hulme C (2003) Molecular Diversity 7:161
Pabba C, Wang H-J, Mulligan SR, Chen Z-J, Stark TM, Gregg BT (2005) Tetrahedron Lett 46:7553
Klapars A, Huang X, Buchwald SL (2002) J Am Chem Soc 124:7421
Tejedor D, Santos-Expósito A, González-Cruz D, Marrero-Tellado JJ, Garcia-Tellado F (2005) J Org Chem 70:1042
Lee JC, Choi HJ, Lee YC (2003) Tetrahedron Lett 44:123
Paul S, Nanda P, Gupta R, Loupy A (2004) Tetrahedron Lett 45:425
Trost BM, Dogra K, Franzini M (2004) J Am Chem Soc 126:1944
Pottorf RS, Chadha NK, Katkevics M, Ozola V, Suna E, Ghane H, Regberg T, Player MR (2003) Tetrahedron Lett 44:175
Kumar R, Selvam C, Kaur G, Chakraborti AK (2005) Synlett, p 1401
Frolov EB, Lakner FJ, Khvat AV, Ivachtchenko AV (2004) Tetrahedron Lett 45:4693
Chakraborti AK, Selvam C, Kaur G, Bhagat S (2004) Synlett, p 851
Phoon CW, Ng PY, Ting AE, Yeo SL, Sim MM (2001) Bioorg Med Chem Lett 11:1647
Kashiyama E, Hutchinson I, Chua MS, Stinson SF, Phillips LR, Kaur G, Sausville EA, Bradshaw TD, Westwell AD, Stevens MFG (1999) J Med Chem 42:4172
Frère S, Thiéry V, Bailly C, Besson T (2003) Tetrahedron 59:773
Frère S, Thiéry V, Besson T (2003) Synth Commun 33:3789
Mu X-J, Zou J-P, Zeng R-S, Wu J-C (2005) Tetrahedron Lett 46:4345
Katritzky AR, Singh SK (2002) J Org Chem 67:9077
Rostamizadeh S, Tajik H, Yazdanfarahi S (2003) Synth Commun 33:113
Baxendale IR, Ley SV, Martinelli M (2005) Tetrahedron 61:5323
Brain CT, Brunton SA (2001) Synlett, p 382
Kiryanov AA, Sampson P, Seed AJ (2001) J Org Chem 66:7925
Wang Y, Sauer DR, Djuric SW (2006) Tetrahedron Lett 47:105
Wang Y, Miller RL, Sauer DR, Djuric SW (2005) Org Lett 7:925
Schulz MJ, Coats SJ, Hlasta DJ (2004) Org Lett 6:3265
Bliznets IV, Vasil'ev AA, Shorshnev SV, Stepanov AE, Lukyanov SM (2004) Tetrahedron Lett 45:2571
Ek F, Manner S, Wistrand L-G, Frejd T (2004) J Org Chem 69:1346
Chetia A, Longchar M, Lekhok KC, Boruah RC (2004) Synlett, p 1309
Bagley MC, Lunn R, Xiong X (2002) Tetrahedron Lett 43:8331
Sainz YF, Raw SA, Taylor RJK (2005) J Org Chem 70:10086
Öhberg L, Westman J (2001) Synlett, p 1296
Legeay J-C, Van den Eynde JJ, Bazureau JP (2005) Tetrahedron 61:12386
Bagley MC, Singh N (2002) Synlett, p 1718
Devi I, Kumar BSD, Bhuyan PJ (2003) Tetrahedron Lett 44:8307
Devi I, Bhuyan PJ (2004) Synlett, p 283
Agarwal A, Chauhan PMS (2005) Tetrahedron Lett 46:1345
Tu S, Miao C, Gao Y, Fang F, Zhuang Q, Feng Y, Shia D (2004) Synlett, p 255
Gorobets NY, Yousefi BH, Belaj F, Kappe CO (2004) Tetrahedron 60:8633
Singh PND, Klima RF, Muthukrishnan S, Murthy RS, Sankaranarayanan J, Stahlecker HM, Patel B, Gudmundsdóttir AD (2005) Tetrahedron Lett 46:4213
Theoclitou M, Robinson LA (2002) Tetrahedron Lett 43:3907
Wilson NS, Sarko CR, Roth GP (2002) Tetrahedron Lett 43:581
Yadav JS, Reddy VS, Rao RS, Naveenkumar V, Nagaiah K (2003) Synthesis, p 1610
Jia C-S, Zhang Z, Tu S-J, Wang G-W (2006) Org Biomol Chem 4:104
Carranco I, Díaz JL, Jiménez O, Vendrell M, Albericio F, Royo M, Lavilla R (2005) J Comb Chem 7:33
Mitra AK, Banerjee K (2003) Synlett, p 1509
Hazarkhani H, Karimi B (2004) Synthesis, p 1239
Saxena I, Borah DC, Sarma JC (2005) Tetrahedron Lett 46:1159
Stadler A, Kappe CO (2001) J Comb Chem 3:624
Xia M, Wang Y (2003) Synthesis, p 262
Tyagarajan S, Chakravarty P (2005) Tetrahedron Lett 46:7889
Bagley MC, Hughes DD, Lubinu MC, Merritt EA, Taylor PH, Tomkinson NCO (2004) QSAR Combi Sci 23:859
Bagley MC, Hughes DD, Taylor PH (2003) Synlett, p 259
Mont N, Teixido J, Borell JI, Kappe CO (2003) Tetrahedron Lett 44:5385
Alexandre F-R, Berecibar A, Besson T (2002) Tetrahedron Lett 43:3911
Liu J-F, Lee J, Dalton AM, Bi G, Yu L, Baldino CM, McElory E, Brown M (2005) Tetrahedron Lett 46:1241
Liu JF, Ye P, Zhang B-L, Bi G, Sargent K, Yu L, Yohannes D, Baldino CM (2005) J Org Chem 70:6339
Liu J-F, Ye P, Sprague K, Sargent K, Yohannes D, Baldino CM, Wilson CJ, Ng S-C (2005) Org Lett 7:3363
Liu J-F, Ye P, Zhang B, Bi G, Sargent K, Yu L, Yohannes D, Baldino CM (2005) J Org Chem 70:10488
López-Cobenas A, Cledera P, Sánchez JD, Pérez-Contreras R, López-Alvarado P, Ramos MT, Avendaño C, Menéndez JC (2005) Synlett, p 1158
Cledera P, Sánchez JD, Caballero E, Avendaño C, Ramos MT, Menéndez JC (2004) Synlett, p 803
Macleod C, Martinez-Teipel BI, Barker WM, Dolle RE (2006) J Comb Chem 8:132
Pérez R, Beryozkina T, Zbruyev OI, Haas W, Kappe CO (2002) J Comb Chem 4:501
Zhao Z, Wisnoski DD, Wolkenberg SE, Leister WH, Wang Y, Lindsley CW (2004) Tetrahedron Lett 45:4873
Lindsley CW, Zhao Z, Leister WH, Robinson RG, Barnett SF, Deborah D-J, Raymond EJ, Hartman GD, Huff JR, Huber HE, Duggan ME (2005) Bioorg Med Chem Lett 15:761
Kim SY, Park KH, Chung YK (2005) Chem Commun, p 1321
Zhang W, Tempest P (2004) Tetrahedron Lett 45:6757
Cho S, Keum G, Kang SB, Han S-Y, Kim Y (2003) Molecular Diversity 6:283
Chang W-J, Yeh W-B, Sun C-M (2003) Synlett, p 1688
Tung C-L, Sun C-M (2004) Tetrahedron Lett 45:1159
Zhao Z, Leister WH, Strauss KA, Wisnoski DD, Lindsley CW (2003) Tetrahedron Lett 44:1123
Peng Y, Song G (2004) Tetrahedron Lett 45:5313
Lee H-K, Rana TM (2004) J Comb Chem 6:504
Seijas JA, Vázquez-Tato MP, Carballido-Reboredo R (2005) J Org Chem 70:2855
Perreux L, Loupy A (2002) Nonthermal Effects of Microwaves in Organic Synthesis. In: Loupy A (ed) Microwaves in Organic Synthesis. Wiley, Weinheim, p 61
Tsukayama M, Kawamura Y, Ishizuka T, Hayashi S, Torii F (2003) Heterocycles 60:2725
Kabalka GW, Mereddy AR (2005) Tetrahedron Lett 46:6315
Besson T, Thiéry V, Frère S (2001) Tetrahedron Lett 42:2791
Laporterie A, Marquié J, Dubac J (2002) Microwave-assisted Reactions on Graphite. In: Loupy A (ed) Microwaves in Organic Synthesis. Wiley, Weinheim, p 219
Acknowledgments
We thank Professor E. Lukevics, Dr. J. Fotins and Dr. R. Zemribo for proof-reading of the manuscript and artist L. Putnina for designing the graphical abstract.
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Suna, E., Mutule, I. (2006). Microwave-assisted Heterocyclic Chemistry. In: Larhed, M., Olofssonq, K. (eds) Microwave Methods in Organic Synthesis. Topics in Current Chemistry, vol 266. Springer, Berlin, Heidelberg . https://doi.org/10.1007/128_058
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DOI: https://doi.org/10.1007/128_058
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