Preparation of Polyfunctional Heterocycles Using Highly Functionalized Aminated Arylmagnesium Reagents as Versatile Scaffolds

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1819-1822

  Lindsay, David M ^a   Dohle, Wolfgang ^a   Jensen, Anne Eeg ^a   Kopp, Felix ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

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Indexed keywords

ARTICLE;

EID: 0001651959     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025597x     Document Type: Article

References (51)

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17. For alternative methods for the preparation of functionalized aryl-magnesium reagents, see: (a) Lee, J.; Velarde-Ortiz, R.; Guijarro, A.; Wurst, J. R.; Rieke, R. D. J. Org. Chem. 2000, 65, 5428. (b) Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2000, 39, 2481. (c) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333.
18. For alternative methods for the preparation of functionalized aryl-magnesium reagents, see: (a) Lee, J.; Velarde-Ortiz, R.; Guijarro, A.; Wurst, J. R.; Rieke, R. D. J. Org. Chem. 2000, 65, 5428. (b) Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2000, 39, 2481. (c) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333.
19. For alternative methods for the preparation of functionalized aryl-magnesium reagents, see: (a) Lee, J.; Velarde-Ortiz, R.; Guijarro, A.; Wurst, J. R.; Rieke, R. D. J. Org. Chem. 2000, 65, 5428. (b) Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2000, 39, 2481. (c) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333.
20. Varchi, G.; Jensen, A. E.; Dohle, W.; Ricci, A.; Cahiez, G.; Knochel, P. Synlett 2001, 477.
21. Functionalized heterocycles can also be prepared using various lithiated aromatic or heterocyclic precursors; see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879. (b) Green, L.; Chander, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453. (c) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 4059. (e) Turck, A.; Ple, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489. For recent metal-mediated indole synthesis, see: (f) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251. (g) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
22. Functionalized heterocycles can also be prepared using various lithiated aromatic or heterocyclic precursors; see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879. (b) Green, L.; Chander, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453. (c) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 4059. (e) Turck, A.; Ple, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489. For recent metal-mediated indole synthesis, see: (f) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251. (g) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
23. Functionalized heterocycles can also be prepared using various lithiated aromatic or heterocyclic precursors; see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879. (b) Green, L.; Chander, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453. (c) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 4059. (e) Turck, A.; Ple, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489. For recent metal-mediated indole synthesis, see: (f) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251. (g) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
24. Functionalized heterocycles can also be prepared using various lithiated aromatic or heterocyclic precursors; see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879. (b) Green, L.; Chander, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453. (c) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 4059. (e) Turck, A.; Ple, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489. For recent metal-mediated indole synthesis, see: (f) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251. (g) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
25. Functionalized heterocycles can also be prepared using various lithiated aromatic or heterocyclic precursors; see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879. (b) Green, L.; Chander, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453. (c) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 4059. (e) Turck, A.; Ple, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489. For recent metal-mediated indole synthesis, see: (f) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251. (g) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
26. Functionalized heterocycles can also be prepared using various lithiated aromatic or heterocyclic precursors; see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879. (b) Green, L.; Chander, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453. (c) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 4059. (e) Turck, A.; Ple, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489. For recent metal-mediated indole synthesis, see: (f) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251. (g) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
27. Functionalized heterocycles can also be prepared using various lithiated aromatic or heterocyclic precursors; see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879. (b) Green, L.; Chander, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453. (c) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149. (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 4059. (e) Turck, A.; Ple, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489. For recent metal-mediated indole synthesis, see: (f) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251. (g) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
28. Compounds 1a-c have been prepared according to literature procedures; see Supporting Information. (a) Sy, W.-W. Synth. Commun. 1992, 22, 3215, (b) Gottlieb, L.; Meyers, A. I. Tetrahedron Lett. 1990, 31, 4723, (c) Meyers, A. I.; Elsworthy, T. R. J. Org. Chem. 1992, 57, 4732, (d) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652, (e) Toste, D.; McNulty, J.; Still, I. W. J. Synth. Commun. 1994, 24, 1617.
29. Compounds 1a-c have been prepared according to literature procedures; see Supporting Information. (a) Sy, W.-W. Synth. Commun. 1992, 22, 3215, (b) Gottlieb, L.; Meyers, A. I. Tetrahedron Lett. 1990, 31, 4723, (c) Meyers, A. I.; Elsworthy, T. R. J. Org. Chem. 1992, 57, 4732, (d) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652, (e) Toste, D.; McNulty, J.; Still, I. W. J. Synth. Commun. 1994, 24, 1617.
30. Compounds 1a-c have been prepared according to literature procedures; see Supporting Information. (a) Sy, W.-W. Synth. Commun. 1992, 22, 3215, (b) Gottlieb, L.; Meyers, A. I. Tetrahedron Lett. 1990, 31, 4723, (c) Meyers, A. I.; Elsworthy, T. R. J. Org. Chem. 1992, 57, 4732, (d) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652, (e) Toste, D.; McNulty, J.; Still, I. W. J. Synth. Commun. 1994, 24, 1617.
31. Compounds 1a-c have been prepared according to literature procedures; see Supporting Information. (a) Sy, W.-W. Synth. Commun. 1992, 22, 3215, (b) Gottlieb, L.; Meyers, A. I. Tetrahedron Lett. 1990, 31, 4723, (c) Meyers, A. I.; Elsworthy, T. R. J. Org. Chem. 1992, 57, 4732, (d) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652, (e) Toste, D.; McNulty, J.; Still, I. W. J. Synth. Commun. 1994, 24, 1617.
32. Compounds 1a-c have been prepared according to literature procedures; see Supporting Information. (a) Sy, W.-W. Synth. Commun. 1992, 22, 3215, (b) Gottlieb, L.; Meyers, A. I. Tetrahedron Lett. 1990, 31, 4723, (c) Meyers, A. I.; Elsworthy, T. R. J. Org. Chem. 1992, 57, 4732, (d) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652, (e) Toste, D.; McNulty, J.; Still, I. W. J. Synth. Commun. 1994, 24, 1617.
33. Compound 2 has been prepared according to literature procedures; see Supporting Information. (a) Sy, W.-W. Synth. Commun. 1992, 22, 3215, (b) Nicolet, B. H.; Ray, W. L. J. Am. Chem. Soc. 1927, 49, 1804.
34. Compound 2 has been prepared according to literature procedures; see Supporting Information. (a) Sy, W.-W. Synth. Commun. 1992, 22, 3215, (b) Nicolet, B. H.; Ray, W. L. J. Am. Chem. Soc. 1927, 49, 1804.
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49. Wang resin attached compound 22 was prepared according to literature procedures starting from compound 1a; see Supporting Information. (a) Laganis, E. D.; Chenard, B. L. Tetrahedron Lett. 1984, 25, 5831, (b) Sheehan, J. C.; Hess, G. P. J. Am. Chem. Soc. 1955, 77, 1067.
50. Wang resin attached compound 22 was prepared according to literature procedures starting from compound 1a; see Supporting Information. (a) Laganis, E. D.; Chenard, B. L. Tetrahedron Lett. 1984, 25, 5831, (b) Sheehan, J. C.; Hess, G. P. J. Am. Chem. Soc. 1955, 77, 1067.
51. 4, filtered and concentrated in vacuo. The crude product was then titurated with a few mL of 1:1 pentane/ether to give 11 as a white powder (224 mg, 53% yield).