Microwave-assisted rapid and selective synthesis of cis- and trans-2,4,5-triarylimidazolines from aromatic aldehydes

Synlett

Volumn , Issue 8, 2003, Pages 1117-1120

  Uchida, Hitoshi ^a   Tanikoshi, Hirofumi ^a   Nakamura, Shuichi ^a   Reddy, Paidi Yella ^b   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

^b Aisin Cosmos R and D Co   (Japan)

Author keywords

Hexamethyldisilazane; Imidazoline; Methanediamine; Microwave; Solvent free

Indexed keywords

2,4,5 TRIPHENYLIMIDAZOLINE; ALDEHYDE; ALUMINUM OXIDE; BENTONITE; BENZALDEHYDE; ETHYLENEDIAMINE DERIVATIVE; HEXAMETHYLDISILAZANE; IMIDAZOLINE DERIVATIVE; MONTMORILLONITE; N,N' BIS(PHENYLMETHYLIDENE)PHENYLMETHANEDIAMINE; REAGENT; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CIS TRANS ISOMERISM; MICROWAVE RADIATION; SYNTHESIS;

EID: 0038729630     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39906     Document Type: Article

References (38)

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5. See for example: (a) Corey, E. J.; Huang, H. C. Tetrahedron Lett. 1989, 30, 5235. (b) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xing, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. (d) Corey, E. J.; DaSilva, J. P.; Virgil, S.; Yuen, P. W.; Conneell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (e) Corey, E. J.; Yu, C. M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878. (f) Zhang, W.; Loebatch, J.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (g) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (h) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296. (i) Corey, E. J.; Imai, N.; Pikul, S. Tetrahedron Lett. 1991, 32, 7517. (j) Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. (k) Corey, E. J.; Sarshar, S.; Lee, D.-H. J. Am. Chem. Soc. 1994, 116, 12089. (l) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616. (m) Corey, E. J.; Sarshar, S.; Azimioara, M. D.; Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851. (n) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
6. See for example: (a) Corey, E. J.; Huang, H. C. Tetrahedron Lett. 1989, 30, 5235. (b) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xing, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. (d) Corey, E. J.; DaSilva, J. P.; Virgil, S.; Yuen, P. W.; Conneell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (e) Corey, E. J.; Yu, C. M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878. (f) Zhang, W.; Loebatch, J.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (g) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (h) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296. (i) Corey, E. J.; Imai, N.; Pikul, S. Tetrahedron Lett. 1991, 32, 7517. (j) Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. (k) Corey, E. J.; Sarshar, S.; Lee, D.-H. J. Am. Chem. Soc. 1994, 116, 12089. (l) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616. (m) Corey, E. J.; Sarshar, S.; Azimioara, M. D.; Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851. (n) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
7. See for example: (a) Corey, E. J.; Huang, H. C. Tetrahedron Lett. 1989, 30, 5235. (b) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xing, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. (d) Corey, E. J.; DaSilva, J. P.; Virgil, S.; Yuen, P. W.; Conneell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (e) Corey, E. J.; Yu, C. M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878. (f) Zhang, W.; Loebatch, J.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (g) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (h) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296. (i) Corey, E. J.; Imai, N.; Pikul, S. Tetrahedron Lett. 1991, 32, 7517. (j) Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. (k) Corey, E. J.; Sarshar, S.; Lee, D.-H. J. Am. Chem. Soc. 1994, 116, 12089. (l) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616. (m) Corey, E. J.; Sarshar, S.; Azimioara, M. D.; Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851. (n) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
8. See for example: (a) Corey, E. J.; Huang, H. C. Tetrahedron Lett. 1989, 30, 5235. (b) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xing, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. (d) Corey, E. J.; DaSilva, J. P.; Virgil, S.; Yuen, P. W.; Conneell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (e) Corey, E. J.; Yu, C. M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878. (f) Zhang, W.; Loebatch, J.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (g) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (h) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296. (i) Corey, E. J.; Imai, N.; Pikul, S. Tetrahedron Lett. 1991, 32, 7517. (j) Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. (k) Corey, E. J.; Sarshar, S.; Lee, D.-H. J. Am. Chem. Soc. 1994, 116, 12089. (l) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616. (m) Corey, E. J.; Sarshar, S.; Azimioara, M. D.; Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851. (n) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
9. See for example: (a) Corey, E. J.; Huang, H. C. Tetrahedron Lett. 1989, 30, 5235. (b) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xing, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. (d) Corey, E. J.; DaSilva, J. P.; Virgil, S.; Yuen, P. W.; Conneell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (e) Corey, E. J.; Yu, C. M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878. (f) Zhang, W.; Loebatch, J.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (g) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (h) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296. (i) Corey, E. J.; Imai, N.; Pikul, S. Tetrahedron Lett. 1991, 32, 7517. (j) Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. (k) Corey, E. J.; Sarshar, S.; Lee, D.-H. J. Am. Chem. Soc. 1994, 116, 12089. (l) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616. (m) Corey, E. J.; Sarshar, S.; Azimioara, M. D.; Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851. (n) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
10. See for example: (a) Corey, E. J.; Huang, H. C. Tetrahedron Lett. 1989, 30, 5235. (b) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xing, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (c) Corey, E. J.; Yu, C. M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. (d) Corey, E. J.; DaSilva, J. P.; Virgil, S.; Yuen, P. W.; Conneell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (e) Corey, E. J.; Yu, C. M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878. (f) Zhang, W.; Loebatch, J.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. (g) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (h) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296. (i) Corey, E. J.; Imai, N.; Pikul, S. Tetrahedron Lett. 1991, 32, 7517. (j) Corey, E. J.; Sarshar, S.; Bordner, J. J. Am. Chem. Soc. 1992, 114, 7938. (k) Corey, E. J.; Sarshar, S.; Lee, D.-H. J. Am. Chem. Soc. 1994, 116, 12089. (l) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1995, 117, 9616. (m) Corey, E. J.; Sarshar, S.; Azimioara, M. D.; Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851. (n) Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
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23. (b) Grigor'ev, S. V.; Voronkov, M. G.; Mirskov, R. G.; Rakhlin, V. I. Russ. J. Gen. Chem. (Engl. Transl.) 2001, 71, 149.
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27. (a) Caddick, S. Tetrahedron 1995, 38, 10403.
28. (b) Loupy, A. Microwave in Organic Synthesis; Wiley: Weinheim, 2002.
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31. Basic, acidic, and neutral alumina showed similar results.
32. Irradiation in the presence of silica gel for 10 min gave 3a in 44% yield together with 2a and other unidentified products, whereas formation of 3a was not observed in the irradiation with alumina for 10 min.
33. Hunter, D. H.; Sim, S. K. J. Am. Chem. Soc. 1969, 91, 6202.
34. (a) Hunter, D. H.; Sim, S. K. Can. J. Chem. 1972, 50, 669.
35. (b) Hunter, D. H.; Sim, S. K. Can. J. Chem. 1972, 50, 678.
36. Irradiation of cis-3a with 1.0 equiv of t-BuOK/t-BuOH for 5 min gave trans-3a quantitatively.
37. 2. The obtained organic solution was concentrated under vacuum to leave a residue, which was purified by silica gel column chromatography (hexane/EtOAc 9:1) to give 164 mg (85%) of cis-3a.
38. Typical Procedure for Preparation of trans-2,4,5-Triphenylimidazoline (trans-3a) from 1a. A mixture of 1a (209 mg, 1.97 mmol), HMDS (620 μL, 480 mg, 2.95 mmol) and, basic alumina (100 mg) was irradiated for 5 min, and then, t-BuOK (77 mg, 0.69 mmol) and DBU (100 μL, 105 mg 0.69 mmol) were added to the mixture which was further irradiated for an additional 5 min. Work-up and purification as described above gave 159 mg (81%) of trans-3a.