Diels-Alder reactions of 2-oxazolidinone dienes in polar solvents using catalysis or non-conventional energy sources

Monatshefte fur Chemie

Volumn 136, Issue 2, 2005, Pages 177-192

  Fuentes, Aydeé ^a   Martínez Palou, Rafael ^a,b   Jiménez Vázquez, Hugo A ^a   Delgado, Francisco ^a   Reyes, Alicia ^a   Tamariz, Joaquín ^a  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^b INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

Author keywords

Ab initio calculations; Cycloadditions; Ionic liquids; Microwaves; Solvent effect

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; ALKADIENE; ALKENE; ISOCYANIC ACID DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; METHANOL; SOLVENT; WATER;

AB INITIO CALCULATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENERGY RESOURCE; MICROWAVE RADIATION; STEREOCHEMISTRY; ULTRASOUND;

EID: 13444261009     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-004-0244-0     Document Type: Article

References (67)

1. (a) Sauer J, Sustmann R (1980) Angew Chem Int Ed Engl 19: 779;
2. (b) Anh NT, Canadell E, Eisenstein O (1978) Tetrahedron 34: 2283;
3. (c) Sustmann R (1971) Tetrahedron Lett 2721;
4. (d) Houk KN, Sims J, Watts CR, Luskus LJ (1973) J Am Chem Soc 95: 7301;
5. (e) Oppolzer W (1991) Comprehensive Organic Synthesis. Trost BM (ed) Pergamon Press, Oxford, vol 5, chapter 4.1;
6. (f) Fringuelli F, Taticchi A (1990) Dienes in the Diels-Alder reaction. Wiley, New York;
7. (g) Fringuelli F, Taticchi A (2002) The Diels-Alder Reaction: Selected Practical Methods. Wiley, Chichester
8. Craig D, Shipman JJ, Fowler RB (1961) J Am Chem Soc 83: 2885
9. (a) House HO, Cronin TH (1965) J Org Chem 30: 1061;
10. (b) Stewart CA Jr (1963) J Org Chem 28: 3320;
11. (c) Mahaim C, Vogel P (1982) Helv Chim Acta 65: 866
12. (a) Fox MA, Cardona R, Kiwiet NJ (1987) J Org Chem 52: 1469;
13. (b) Tripathy R, Franck RW, Onan KD (1988) J Am Chem Soc 110: 3257;
14. (c) Martin JG, Hill RK (1961) Chem Rev 61: 537
15. Argile A, Ruasse M-F (1980) Tetrahedron Lett 21: 1327
16. (a) Dias LC (1997) J Braz Chem Soc 8: 289;
17. (b) Hollis TK, Odenkirk W, Robinson NP, Whelan J, Bosnich B (1993) Tetrahedron 49: 5415
18. (a) Kong S, Evanseck JD (2000) J Am Chem Soc 122: 10418 and references cited therein;
19. (b) Zhao H, Malhotra SV (2002) Aldrichimica Acta 35: 75;
20. (c) Varma RS, Namboodiri VV (2001) Pure Appl Chem 73: 1309;
21. (d) Grieco PA (1991) Aldrichimica Acta 24: 59;
22. (e) Wasserscheid P, Keim W (2000) Angew Chem Int Ed 39: 3772;
23. (f) Breslow R, Maitra U (1984) Tetrahedron Lett 25: 1239;
24. (g) Welton T (1999) Chem Rev 99: 2071;
25. (h) Khadilkar BM, Rebeiro GL (2002) Org Proc Res Dev 6: 826
26. (a) Microwaves in Organic Synthesis (2002) Loupy A (ed), Wiley-VCH, Weinheim;
27. (b) Hayes BL (2002) Microwave Synthesis: Chemistry at the Speed of Light. CEM Publishing;
28. (c) Ley SV, Low CMR (1989) Ultrasound in Synthesis. Springer, Berlin;
29. (d) Mason TJ, Luche J-L (1997) Ultrasound as a Tool for Synthetic Chemists; and Mingos DMP, Wittaker AG (1997) Microwave Dielectric Heating Effects in Organic Synthesis. In: Eldik RV, Colin DH (eds) Chemistry under Extreme on non-Classical Conditions. Wiley, New York, p 317 and 479;
30. (d) Mason TJ, Luche J-L (1997) Ultrasound as a Tool for Synthetic Chemists; and Mingos DMP, Wittaker AG (1997) Microwave Dielectric Heating Effects in Organic Synthesis. In: Eldik RV, Colin DH (eds) Chemistry under Extreme on non-Classical Conditions. Wiley, New York, p 317 and 479;
31. (e) Einhorn C, Einhorn J, Luche J-L (1989) Synthesis 787;
32. (f) Loupy A, Petit A, Hamelin J, Texier-Boullet F, Jacquault P, Mathé D (1998) Synthesis 1213;
33. (g) Leadbeater NE, Torenius HM (2002) J Org Chem 67: 3145
34. (a) Hernández R, Sánchez JM, Gómez A, Trujillo G, Abortes R, Zepeda LG, Bates RW, Tamariz J (1993) Heterocycles 36: 1951;
35. (b) Mandal AB, Gómez A, Trujillo G, Méndez F, Jiménez HA, Rosales MJ, Martínez R, Delgado F, Tamariz J (1997) J Org Chem 62: 4105
36. Martínez R, Jiménez-Vázquez HA, Reyes A, Tamariz J (2002) Helv Chim Acta 85: 464
37. Martínez R, Jiménez-Vázquez HA, Delgado F, Tamariz J (2003) Tetrahedron 59: 481
38. Mandal AB, Delgado F, Tamariz J (1998) Synlett 87
39. Zempoalteca A, Tamariz J (2002) Heterocycles 57: 259
40. We have previously described the preparation of dienes 5a and 5b: Benavides A, Martínez R, Jiménez-Vázquez HA, Delgado F, Tamariz J (2001) Heterocycles 55: 469
41. Reyes A, Aguilar R, Muñoz AH, Zwick J-C, Rubio M, Escobar J-L, Soriano M, Toscano R, Tamariz J (1990) J Org Chem 55: 1024
42. Houk KN (1975) Acc Chem Res 8: 361
43. (a) Eisenstein O, Lefour JM, Anh NT, Hudson RF (1977) Tetrahedron 33: 523;
44. (b) Houk KN (1973) J Am Chem Soc 95: 4092;
45. (c) Alston PV, Ottenbrite RM, Guner OF, Shillady DD (1986) Tetrahedron 42: 4403;
46. (d) Spino C, Rezaei H, Dory YL (2004) J Org Chem 69: 757 and references cited therein
47. Dewar MJS, Zoebisch EG, Healy EF, Stewart JPP (1985) J Am Chem Soc 107: 3902
48. RHF/3-21G and 6-31G* calculations were performed using MacSpartan [19a] and Gaussian 94 [19b]. (a) MacSpartan, v 1.0, Wave Function Inc., 18401 Von Karman, Suite 370, Irvine, CA 92715; (b) Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Reploge ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JP, Head-Gordon M, Gonzalez C, Pople JA (1995) Gaussian, Inc, Pittsburgh
49. RHF/3-21G and 6-31G* calculations were performed using MacSpartan [19a] and Gaussian 94 [19b]. (a) MacSpartan, v 1.0, Wave Function Inc., 18401 Von Karman, Suite 370, Irvine, CA 92715; (b) Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Reploge ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JP, Head-Gordon M, Gonzalez C, Pople JA (1995) Gaussian, Inc, Pittsburgh
50. Fleming I (1976) Frontier Orbitals and Organic Chemical Reactions. Wiley, Chichester
51. Bachler V, Mark F (1976) Theoret Chim Acta 43: 121
52. Jiménez-Vázquez HA, Ochoa ME, Zepeda LG, Modelli A, Jones D, Mendoza JA, Tamariz J (1997) J Phys Chem A 101: 10082
53. García JI, Mayoral JA, Salvatella L (2000) Acc Chem Res 33: 658
54. (a) Houk KN (1970) Tetrahedron Lett 2621;
55. (b) Stephenson LM, Smith DE, Current SP (1982) J Org Chem 47: 4170;
56. (c) Ginsburg D (1983) Tetrahedron 39: 2095;
57. (d) Güner OF, Ottenbrite RM, Shillady DD, Alston PV (1988) J Org Chem 53: 5348;
58. (e) Singleton DA (1992) J Am Chem Soc 114: 6563;
59. (f) Loncharich RJ, Brown FK, Houk KN (1989) J Org Chem 54: 1129
60. García JI, Martínez-Merino V, Mayoral JA, Salvatella L (1998) J Am Chem Soc 120; see also: Yamabe S, Minato T (2002) J Org Chem 65: 1830
61. García JI, Martínez-Merino V, Mayoral JA, Salvatella L (1998) J Am Chem Soc 120; see also: Yamabe S, Minato T (2002) J Org Chem 65: 1830
62. (a) Caramella P, Quadrelli P, Toma L (2002) J Am Chem Soc 124: 1130;
63. (b) Quadrelli P, Romano S, Toma L, Caramella P (2003) J Org Chem 68: 6035;
64. (c) Birney DM, Houk KN (1990) J Am Chem Soc 112: 4127
65. Toma S. Romano, Quadrelli P, Caramella P (2001) Tetrahedron Lett 42: 5077. For an updated interpretation of the dimerization of methacrolein, see Ref 26a
66. Web page: www.sevmexico.com
67. SHELXTL (1995) v 5.03, Siemens Energy & Automation, Germany