Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

Tetrahedron

Volumn 63, Issue 2, 2007, Pages 337-346

  Pospíšil, Jiří ^a   Potáček, Milan ^a  

^a MASARYK UNIVERSITY   (Czech Republic)

Author keywords

1,3 Dipolar cycloaddition; Azomethine ylides; Intramolecular cycloaddition; Microwave assisted synthesis; Solvent free synthesis

Indexed keywords

ALKENE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIPOLE; GEOMETRY; ISOMERIZATION; MICROWAVE IRRADIATION; OBSERVATION; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS;

EID: 33751541673     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.074     Document Type: Article

References (57)

1. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765-2809
2. Eberbach W. Science of Synthesis, Houben-Weyl Methods of Molecular Transformation (2004), Thieme, Stuttgart Vol. 27, pp 441-498
3. Harwood L.M., and Vickers R.J. In: Padwa A., and Pearson W.H. (Eds). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (2003), Wiley, New York, NY 169
4. Najera C., and Sansano J.M. Curr. Org. Chem. 7 (2003) 1105-1150
5. Huisgen R. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry Vol. 1 (1984), Wiley, New York, NY 1
6. Wade P. In: Trost B.M., and Flemming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford 1111-1168
7. Tanaka K., and Toda F. Chem. Rev. 100 (2000) 1025-1074
8. De la Hoz A., Diaz-Ortiz A., and Langa F. In: Loupy A. (Ed). Microwaves in Organic Synthesis (2002), Wiley-VCH GmbH & KGaA, Weinheim, Germany 295-343
9. Rossini M., Budriesi R., Bixel M.G., Bolognesi M.L., Chiarini A., Hucho F., Krogsgaard-Larsen P., Mellor A., Minarini I.R., Tumiatti V., Usherwood P.N.R., and Melchiorre C. J. Med. Chem. 42 (1999) 5212-5223
10. Mahmud H., Lovely C.J., and Rasika Dias H.V. Tetrahedron 57 (2001) 4095-4105
11. Witherup K.M., Ransom R.M., Graham A.C., Anderson P.S., Pitzenberger S.M., and Varga S.L. J. Am. Chem. Soc. 117 (1995) 6682-6685
12. Confalone P.N., and Huie E.M. J. Am. Chem. Soc. 106 (1984) 7175-7178
13. Kanemasa S., Sakamoto K., and Tsuge O. Bull. Chem. Soc. Jpn. 62 (1989) 1960-1968
14. Martin S.F., and Cheavens T.H. Tetrahedron Lett. 30 (1989) 7017-7020
15. Grigg R., Savic V., and Thornton-Pett M. Tetrahedron 53 (1997) 10633-10642
16. See Ref. 6c;
17. Gong Y.-D., Najdi S., Olmstead M.M., and Kurth M.J. J. Org. Chem. 63 (1998) 3081-3086
18. Bashiardes G., Safir I., Mohamed A.S., Barbot F., and Laduranty J. Org. Lett. 5 (2003) 4915-4918
19. Bashiardes G., Safir I., Barbot F., and Laduranty J. Tetrahedron Lett. 44 (2003) 8417-8420
20. (a) See Ref. 6g;
21. Zhang W., Lu Y., and Geib S. Org. Lett. 7 (2005) 2269-2272
22. Pospíšil J., and Potáček M. Eur. J. Org. Chem. (2004) 710-716 Other microwave-assisted solvent-free reactions of azomethine ylides:
23. Jayashankaran J., Manian R.D.R.S., Venkatesan R., and Raghunathan R. Tetrahedron 61 (2005) 5595-5598
24. Jayashankaran J., Manian R.D.R.S., and Raghunathan R. Tetrahedron Lett. 45 (2004) 7303-7305
25. Azizian J., Karimi A.R., Dastkhan R., Mohammadi A.A., and Mohammadizadeh M.R. J. Chem. Res. (2004) 347-349
26. Trávníček M., and Potáček M. ARKIVOC (2001) 156-163
27. Cheng Q., Zhang W., Tagami Y., and Oritani T. J. Chem. Soc., Perkin Trans. 1 (2001) 452-456
28. Azizian J., Asadi A., and Jadidi K. Synth. Commun. 31 (2001) 2727-2733
29. Langa F., De la Cruz P., De la Hoz A., Espildora E., Cossio F.P., and Lecea B. J. Org. Chem. 65 (2000) 2499-2507
30. Fraga-Dubreuil J., Cherouvrier J.R., and Bazureau J.P. Green Chem. 2 (2000) 226-229
31. Lerestif J.M., Perrocheau J., Tonnard F., Bazureau J.P., and Hamelin J. Tetrahedron 51 (1995) 6757-6774
32. This very polar fraction, which sticks on the silica gel, presented a very complicated mixture of probably decomposed reaction intermediates, which was not possible to analyze. At first, we have expected the formation of product of the Claisen rearrangement, however, this product was not observed in the reaction mixture.
33. Jacob J., Chia L.H.L., and Boey F.Y.C. J. Mater. Sci. 30 (1995) 5321-5327
34. Laurent R., Laporterie A., Dubac J., Berlan J., Lefeuvre R., and Audhuy M. J. Org. Chem. 57 (1992) 7099-7102
35. Strauss C.R., and Trainor R.W. Aust. J. Chem. 48 (1995) 1665-1671
36. Barghust D.R., and Mingos D.M.P. J. Chem. Soc., Chem. Commun. (1992) 674-677
37. Taft R.W., and Bordwell F.G. Acc. Chem. Res. 21 (1988) 463-469
38. The condensation of the water was observed above the open reaction vessel in the course of the reaction.
39. This reaction is possible to extend to other aldehydes as well as N-alkyl 2-alkylaminoacetamides and represents an elegant way for the preparation of 1,2,3-trialkyl substituted imidazolin-4-ones. Desired compounds are formed generally in 5 min (200 °C, μW) in 90-96% yields. Interestingly, the reaction is possible to carry out under the classical heating with comparable yields, however, the reaction times are longer (30 min). See:. Pospíšil J., and Potáček M. Heterocycles 63 (2004) 1165-1173
40. Interestingly, no products of the intermolecular reaction (dimers, trimers,...) were observed in the reaction mixture (GC-MS).
41. a of the equivalent hydrogen atom attached to the carbon next to ester group is ∼28. The values are valid in DMSO (see Ref. 11).
42. Carruthers W. Cycloaddition Reactions in Organic Synthesis (1990), Pergamon, Oxford
43. Stabilities of aldehyde 4, amines 18a-c and cycloadducts 20a-c under the reaction conditions were tested and all the compounds were reisolated in >85% yield. Typical temperature profile of the reaction is presented in Graph S-1 and can be found in Supplementary data.
44. Grigg R., Gunaratane H.Q.N., and Kemp J. J. Chem. Soc., Perkin Trans. 1 (1984) 41-46
45. Grigg R. Chem. Soc. Rev. 16 (1987) 89-121
46. Fleming I. Frontier Orbitals and Organic Chemical Reactions (1976), Wiley, Chichester, England p 96
47. Houk K.N., Paddon-Row M., Rondan N.G., Wu Y.-D., Brown F.K., Spellmeyer D., Metz J.T., Li Y., and Loncharich R.J. Science 231 (1986) 1108-1117
48. Hammond G.S. J. Am. Chem. Soc. 77 (1955) 334-338
49. 1H NMR. See Supplementary data Graph S-2.
50. Tam W. J. Org. Chem. 66 (2001) 5113-5123
51. Weaver W.E., and Whaley W.M. J. Am. Chem. Soc. 69 (1947) 515-516 and 1144-1145
52. Swensen A.D., and Weaver W.E. J. Am. Chem. Soc. 70 (1948) 4060-4061
53. Travníček M., and Potáček M. Molecules 4 (1999) 238-244
54. Saha U.K., and Roy R. J. Chem. Soc., Chem. Commun. (1995) 2571-2573
55. Shimizu T., Hayashi Y., Kitora Y., and Teramura K. Bull. Chem. Soc. Jpn. 55 (1982) 2450-2455
56. Maruoka K., Akaruta M., Saito S., Susumu O., and Yamamoto H. J. Am. Chem. Soc. 116 (1994) 6153-6158
57. Kende, A. S.; Fludzinski, P. Organic Syntheses; Wiley: New York, NY, 1990; Collect. Vol. 7, p 221.