Enhancing stereochemical diversity by means of microwave irradiation in the absence of solvent: Synthesis of highly substituted nitroproline esters via 1,3-dipolar reactions

Molecular Diversity

Volumn 7, Issue 2-4, 2003, Pages 175-180

  Díaz Ortiz, Angel ^a   De La Hoz, Antonio ^a   Herrero, M Antonia ^a   Prieto, Pilar ^a   Sánchez Migallón, Ana ^a   Cossío, Fernando P ^b   Arrieta, Ana ^b   Vivanco, Silvia ^b   Foces Foces, Concepción ^c  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

1,3 dipolar cycloaddition; Azomethine ylide; Microwaves; Proline esters; Solventless

Indexed keywords

ALPHA AMINOESTER; AMINO ACID; AMPHOLYTE; ESTER; IMINE; NITROPROLINE ESTER; NITROSTYRENE; PROLINE; PYRROLIDINE DERIVATIVE; SOLVENT; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

1,3 DIPOLAR REACTION; ARTICLE; CHEMICAL REACTION; CYCLOADDITION; HEATING; ISOMERISM; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CHEMISTRY, ORGANIC; ESTERS; IMINES; MICROWAVES; MODELS, CHEMICAL; MODELS, MOLECULAR; NAPHTHALENESULFONATES; NITROGEN; PROLINE; SOLVENTS; STEREOISOMERISM;

EID: 0345825853     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006799.01924.2e     Document Type: Article

References (36)

1. Maclean, D., Baldwin, J. J., Ivanov, V. T., Kato, Y., Shaw, A., Schneider, P. and Gordon, A. E. M., Glossary of terms used in combinatorial chemistry, J. Comb. Chem., 2 (2000) 562-578.
2. Hermkens, P. H. H., Ottenheijm, H. C. J. and Rees, D. C., Solid phase organic reactions: A review of the recent literature, Tetrahedron, 52 (1996) 4527-4554.
3. Hermkens, P. H. H., Ottenheijm, H. C. J. and Rees, D. C., Solid phase organic reactions II: A review of the literature Nov 95-Nov 96, Tetrahedron, 53 (1997) 5643-5678.
4. Dolle, R. E. and Nelson, K. H., Comprehensive survey of combinatorial library synthesis: 1998, J. Comb. Chem., 1 (1998) 235-282.
5. Dolle, R. E., Comprehensive survey of combinatorial library synthesis: 1999, J. Comb. Chem., 2 (1999) 383-433.
6. Loupy, A., Petit, A., Hamelin, J., Texier-Boullet, F., Jacquault, P. and Mathé, D., New solvent-free organic synthesis using focused microwaves, Synthesis, (1998) 1213-1234.
7. Lidström, P., Tierney, J., Wathey, B. and Westman, J., Microwave assisted organic synthesis - A review, Tetrahedron, 57 (2001) 9225-9283.
8. Varma, R. S., Solvent-free organic syntheses using supported reagents and microwave irradiation, Green Chem., 1 (1999) 43-55.
9. Strauss, C. R., A combinatorial approach to the development of enviromentally benign organic chemical preparations, Aust. J. Chem., 52 (1999) 83-96.
10. Loupy, A. (ed.), Microwaves in Organic Synthesis, Wiley-VCH, Weinheim (FRG), 2002.
11. Bose, A. K., Banik, B. K. and Manhas, M. S., Stereocontrol of β-lactam formation using microwave irradiation, Tetrahedron Lett., 36 (1995) 213-216.
12. 70 under microwave irradiation, J. Org. Chem., 65 (2000) 2499-2507.
13. Kappe, C. O., High-speed combinatorial synthesis utilizing microwave irradiation, Curr. Opin. Chem. Biol., 6 (2002) 314-320.
14. Larhed, M. and Hallberg, A., Microwave-assisted high-speed chemistry: A new technique in drug discovery, Drug Disc. Today, 6 (2001) 406-416.
15. Lew, A., Krutzik, P. O., Hart, M. E. and Chamberlin, A. R., Increasing rates of reactions: Microwave-assisted organic synthesis for combinatorial chemistry, J. Comb. Chem., 4 (2002) 95-105.
16. Grigg, R. and Kemp, J., 1,3-Dipolar cycloaddition reactions of imines of α-amino acid esters: X-ray crystal and molecular structure of methyl 4-(2-furyl)-2,7-diphenyl-6,8-dioxo-3,7-diazabicyclo[3.3.0]octane-2-carboxylate, J. Chem. Soc., Chem. Commun., (1978) 109-111.
17. Grigg, R. and Kemp, J., X = Y - ZH systems as potential 1,3-dipoles. The stereochemistry and regiochemistry of cycloaddition reactions of imines of α-amino-acid esters, Tetrahedron Lett., 21 (1980) 2461-2464.
18. Tsuge, O. and Kanemasa, S., 'Recent Advances in Azomethine Ylide Chemistry', in A. R. Katritzky (ed.), Advances in Heterocyclic Chemistry, Vol. 45, Academic Press, San Diego, 1989, pp. 231-349.
19. Lown, J. W., in A. Padwa (ed.), 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, Wiley, New York, 1984, pp. 653-732.
20. Grigg, R., Prototopic routes to 1,3- and 1,5-dipoles, and 1,2-ylides: Applications to the synthesis of heterocyclic compounds, Chem. Soc. Rev., 16 (1987) 89-121.
21. Padwa, A., Chen, Y. Y., Chiacchio, U. and Dent, W., Diastereofacial selectivity in azomethine ylide cycloaddition reactions derived from chiral α-cyanoaminosilanes, Tetrahedron, 41 (1985) 3529-3535, and references therein.
22. Schwarz, R. T. and Datema, R., Inhibitors of trimming: New tools in glycoprotein research, Trends Biochem. Sci., 9 (1984) 32-34.
23. Fleet, G. W., Amino-sugar derivatives and related compounds as glycosidase inhibitors, Top. Med. Chem., 65 (1988) 149-162.
24. Jäger, V. and Hümmer W., Cyclization of N-protected 1-amino-4-pentene-2,3-diols to lyxo-configurated deoxyimino sugars (cis-dihydroxypyrrolidines): Synthesis of potential glycosidase inhibitors, Angew. Chem., Int. Ed. Engl., 29 (1990) 1171-1173.
25. Marx, M. A., Grillot, A. L., Louer, C. T., Beaver, K. A. and Barlett, P. A., Synthetic design for combinatorial chemistry. Solution and polymer-supported synthesis of polycyclic lactams by intramolecular cyclization of azomethine ylides, J. Am. Chem. Soc., 119 (1997) 6153-6167.
26. Fokas, D., Ryan, W. J., Casebier, D. S. and Coffen, D. L., Solution phase synthesis of a spiro[pyrrolidine-2,3′-oxindole] library via a three component 1,3-dipolar cycloaddition reaction, Tetrahedron Lett., 39 (1998) 2235-2238.
27. Murphy, M. M., Schullek, J. R., Gordon, E. M. and Gallop, M. A., Combinatorial organic synthesis of highly functionalizated pyrrolidines: Identification of a potent angiotensin converting enzyme inhibitor from a mercaptoacyl proline library, J. Am. Chem. Soc., 117 (1995) 7029-7030.
28. Hollinshead, S. P., Stereoselective synthesis of highly functionalized pyrrolidines via 1,3-dipolar cycloaddition reaction on a solid support, Tetrahedron Lett., 37 (1996) 9157-9160.
29. Bicknell, A. J. and Hird, N. W., Synthesis of a highly functionalized rigid template by solid phase azomethine ylide cycloaddition, Bioorg. Med. Chem. Lett., 6 (1996) 2441-2444.
30. Hamper, B. C., Dukesherer, D. R. and South, M. S., Solid-phase synthesis of proline analogs via a three component 1,3-dipolar cycloaddition. Tetrahedron Lett., 37 (1996) 3671-3674.
31. Gong, Y. D., Nadji, S., Olmstead, M. and Kurth, M. J., Solid-phase synthesis: Intramolecular azomethine ylide cycloaddition (→ proline) and carbanilide cyclization (→ hydantoin) reactions, J. Org. Chem., 63 (1998) 3081-3086.
32. De la Hoz, A., Díaz-Ortiz, A., Moreno, A. and Langa, F., Cycloadditions under microwave irradiation conditions: Methods and applications, Eur. J. Org. Chem., (2000) 3659-3673.
33. Ayerbe, M., Arrieta, A., Cossío, F. P. and Linden, A., Stereocontrolled synthesis of highly substituted proline esters vis [3+2] cycloadditions between N-metalated azomethine ylides and nitroalkenes. Origins of the metal effect on the stereochemical outcome, J. Org. Chem., 63 (1998) 1795-1805.
34. General procedure: A mixture of the imine (1 equiv) and the fl-nitrostyrene (1 equiv) was irradiated in a modified Prolabo MX350 microwave reactor at the power and for the time indicated in Table 1. The crude product was purified by silicagel flash column chromatography using hexane/ethyl acetate as the eluent.
35. Vivanco, S., Lecea, B., Arrieta, A., Prieto, P., Morao, I., Linden, A. and Cossío, F. P., Origins of the loss of concertedness in pericyclic reactions: Theoretical prediction and direct observation of stepwise mechanisms in [3+2] thermal cycloadditions, J. Am. Chem. Soc., 122 (2000) 6078-6092.
36. Beauseleil, E. and Lubell, W. D., Steric effects on the amide isomer equilibrium of prolyl peptides. Synthesis and conformational analysis of N-acetyl-5-terct-butylproline N'-methylamides, J. Am. Chem. Soc., 118 (1996) 12902-12908.