Microwave-assisted intramolecular huisgen cycloaddition of azido alkynes derived from α-amino acids

Journal of Organic Chemistry

Volumn 74, Issue 3, 2009, Pages 1314-1321

  Balducci, Evita ^a   Bellucci, Luca ^a   Petricci, Elena ^a   Taddei, Maurizio ^a   Tafi, Andrea ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO STUDIES; CYCLIC POLYESTERS; CYCLOADDUCT; HUISGEN CYCLOADDITION; INTERMOLECULAR CYCLOADDITION; MICROWAVE DIELECTRIC HEATING; MICROWAVE-ASSISTED; PEPTIDOMIMETICS; POTENTIAL ENERGY PROFILES; PRIMARY AMINES; PROPARGYL; REACTION PATHWAYS; RING OPENINGS;

ACETYLENE; AMIDES; AMINATION; AMINES; AMINO ACIDS; ESTERIFICATION; MICROWAVES; ORGANIC ACIDS;

ESTERS;

[1,2,3]TRIAZOLO[5,1 C][1,4]OXAZIN 6 ONE DERIVATIVE; ALKYNE DERIVATIVE; ALPHA AZIDO AMIDE DERIVATIVE; ALPHA AZIDO PROPARGYLESTER DERIVATIVE; AMIDE; AMINO ACID DERIVATIVE; AZIDO ALKYNE DERIVATIVE; ESTER DERIVATIVE; PEPTIDOMIMETIC AGENT; POLYESTER; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; MICROWAVE RADIATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SUBSTITUTION REACTION;

ALKYNES; AMIDES; AMINO ACIDS; AZIDES; CYCLIZATION; MICROWAVES; STEREOISOMERISM; TRIAZOLES;

EID: 64549088984     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802463r     Document Type: Article

References (40)

1. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
2. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51. Gil, M. V.; Arévalo, M. J.; López, O. Synthesis 2007, 1589.
3. Kolb, H.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128. Vocadlo, D. J.; Bertozzi, C. R. Angew Chem. Int. Ed. 2004, 43, 5338. Sawa, M.; Hsu, T.-L.; Itoh, T.; Sugiyama, M.; Hanson, S. R.; Vogt, P. K.; Wong, C.-H. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12371.
4. For example, see: (a) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686.
5. (b) Brik, A.; Muldoon, J.; Lin, Y.-C.; Elder, J. H.; Goodsell, D. S.; Olson, A. J.; Fokin, V. V.; Sharpless, B.; Wong, C.-H. ChemBioChem 2003, 4, 1246.
6. (c) Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535.
7. (d) Burley, G. A.; Gierlich, J.; Moid, M. R.; Nir, H.; Tal, S.; Eichen, Y.; Carell, T. J. Am. Chem. Soc. 2006, 128, 1398.
8. Zhang, L.; Chen, X.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998.
9. Rasmussen, L. K.; Boren, B. C.; Fokin, V. V. Org. Lett. 2007, 9, 5337. For the synthesis of the catalyst see:Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc. 1990, 112, 5166.
10. For an approach to regioselective intermolecular Huisgen reaction with internal alkynes using the Ru catalyst, see: Majireck, M. M.; Weinreb, S. M. J. Org. Chem. 2006, 71, 8680.
11. Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081.
12. Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2006, 8, 4145. Turner, R. A.; Oliver, A. G.; Lokey, R. S. Org. Lett. 2007, 9, 5011. Looper, R. E.; Pizzirani, D.; Schreiber, S. L. Org. Lett. 2006, 8, 2063.
13. Angell, Y.; Burgess, K. J. Org. Chem. 2005, 70, 9595.
14. For examples of intramolecular formation of 1,2,3-triazoles not oriented to the regiocontrolled synthesis of substituted triazoles, see: Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. Thomas, A. W. Bioorg. Med. Chem. Lett. 2002, 12, 1881. Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. Tetrahderon Lett. 2004, 45, 8429. Hotha, S.; Anegundi, R. I.; Natu, A. A. Tetrahedron Lett. 2005, 46, 4585. Mohapatra, D. K.; Maity, P. K.; Gonnade, R. G.; Chorghade, M. S.; Gurjar, M. K. Synlett 2007, 1893. Oliva, A. I.; Christmann, U.; Font, D.; Cuevas, F.; Ballester, P.; Buschmann, H.; Torrens, A.; Yenes, S.; Pericas, M. A. Org. Lett, 2008, 10, 1617. Sudhir, V. S.; Baig, R. B. N.; Chandresekaran, S. Eur. J. Org. Chem. 2008, 2423. For one example of intramolecular reaction appied to the synthesis of a triazole amino acid as peptide turn inducers, see: Pokorski, J. K.; Miller Jenkins, L. M.; Feng, H.; Durell, S. R.; Bai, Y.; Appella, D. H. Org. Lett. 2007, 9, 2381.
15. Lundquist, J. T., IV.; Pelletier, J. C. Org. Lett. 2001, 3, 781.
16. Huisgen, R. Angew. Chem. 1963, 75, 604.
17. 1H NMR and MS spectra fully coherent with the proposed structure.
18. Data recovered by analysis of the mass spectra of all the components of the reaction mixture.
19. Zhao, H.; Sanda, F.; Matsuda, T. Macromolecules 2004, 37, 8888. DMTMM: 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4- methylmorpholinium chloride. See: Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 277. DMTMM is commercially available from Acros Organics.
20. When MeCN alone was used as the solvent, the solution did not reach the temperature required for cycloaddition. When ionic liquid was employed in order to increase the internal temperature, cycoaddition did not occur. (18) HPLC analysis with Chiral Column Chiralpack 1B 0.46 × 15 cm.
21. The yields reported in the scheme were obtained exclusively when the vial containing all the reagents was submitted to MW heating. When the classical procedure of succession in reagent addition was followed, very low yields were obtained at room temperature, whereas MW heating (after addition of benzyl bromide) provided the dibenzyl derivative 42.
22. Compound 27 was obtained in 70% ee, the same of the starting compound 19. When lactam hydrolysis was attempted in oil bath at 100 °C, more then 24 h were required to obtain 75% yields of 19.
23. For the Cu-catalyzed synthesis of triazole-containing amino acids, see: Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134.
24. Although it is possible, no applications of intramolecular cycloaddition to the synthesis of trisubstituted triazoles have been reported until now. For one example of the synthesis of substituted bicyclic triazole via ring opening of aziridine-propargylic derivatives, see: (a) Kim, M. S.; Yoon, H. J.; Lee, B. K.; Known, J. H.; Lee, W. K.; Kim, Y.; Ha, H.-J. Synlett 2005, 2187.
25. (b) Yanai, H.; Taguchi, T. Tetrahedron Lett. 2005, 46, 8639.
26. Bieber, L. W.; da Silva, M. F. Tetrahedron Lett. 2007, 48, 7088.
27. Comparable yields were observed by heating in succession of 20 min irradiation periods for 2 h overall.
28. Although not described here, double-bond functionalization is possible, for example, by oxidative hydroboration, cross-methathesis, or hydroformylation.
29. Compound 43 was prepared but its cyclization to 44 did not occur under the reaction conditions explored for compound 2.
30. For DFT prediction of Cu-catalyzed synthesis of triazole, see: Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.
31. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 1, 4-1347.
32. Aparicio-Martinez, S.; Hall, K. R.; Balbuena, P. B. J. Phys. Chem. A 2006, 110, 9183.
33. The activation barrier for the amide was greater than the activation barrier of the ester. However, the cycloaddition reaction exhibits the same magnitude of energy; therefore, at experimental condition of both reactions, we can exclude a discrimination through kinetic effects. It is important to point out that calculations are performed in vacuo but that the presence of the solvent should stabilize the cis amide conformer. See: Fisher, G. Chem. Soc. Rev. 2000, 29, 119-127.
34. Hassinen, T.; Peräkylä, M. J. Comput. Chem. 2001, 22, 1229.
35. The Massively Parallel Quantum Chemistry Program" (MPQC), Version 2.3.1. Janssen, C. L.; Nielsen, I. B.; Leininger, M. L.; Valeev, E. F.; Kenny, J. P.; Seidl, E. T. Sandia National Laboratories, Livermore, CA, 2008.
36. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
37. Schaftenaar, G.; Noordik, J. H. J. Comput. Aided. Mol. Des. 2000, 14, 123.
38. Humphrey, W.; Dalke, A.; Schulten, K. J. Molec. Graphics 1996, 14, 33.
39. Bofill, J. M. J. Comput. Chem. 1994, 15,1.
40. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.