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Publicly Available Published by De Gruyter May 30, 2010

Synthesis of heterocycles via alkoxyallenes

  • Tilman Lechel and Hans-Ulrich Reissig

Lithiated alkoxyallenes are very versatile components for the synthesis of heterocycles such as furans, pyrroles, and 1,2-oxazines, easily allowing the preparation of natural products via these heterocyclic intermediates. A surprising three-component synthesis of N-acylated enaminones allowed the synthesis of highly functionalized 4-hydroxypyridines, 5-acetyloxazoles, and pyrimidines. All these heterocyclic products are ready for further functionalizations, in particular for palladium-catalyzed reactions, leading to libraries of new interesting heterocycles.


Conference

International Congress on Heterocyclic Chemistry (ICHC-22), International Congress on Heterocyclic Chemistry, ICHC, Heterocyclic Chemistry, 22nd, St John's, Newfoundland and Labrador, Canada, 2009-08-02–2009-08-07


References

1a 10.1055/s-1993-25823, R. Zimmer. Synthesis 165 (1993).Search in Google Scholar

1b 10.1002/jhet.5570370316, H.-U. Reissig, S. Hormuth, W. Schade, M. Okala Amombo, T. Watanabe, R. Pulz, A. Hausherr, R. Zimmer. J. Heterocycl. Chem.37, 597 (2000).Search in Google Scholar

1c 10.1351/pac200274010175, H.-U. Reissig, W. Schade, M. G. Okala Amombo, R. Pulz, A. Hausherr. Pure Appl. Chem.74, 175 (2002).Search in Google Scholar

1d R. Zimmer, H.-U. Reissig. In Modern Allene Chemistry, N. Krause, A. S. K. Hashmi (Eds.), pp. 425–492, Wiley-VCH, Weinheim (2004).Search in Google Scholar

1e 10.1021/ar800011h, M. Brasholz, H.-U. Reissig, R. Zimmer. Acc. Chem. Res.42, 45 (2009).Search in Google Scholar

1f 10.1039/b914356d, F. Pfrengle, H.-U. Reissig. Chem. Soc. Rev.39, 549 (2010).Search in Google Scholar

2 10.1135/cccc2009012, V. Prisyazhnyuk, M. Jachan, I. Brüdgam, R. Zimmer, H.-U. Reissig. Collect. Czech. Chem. Commun.74, 1069 (2009).Search in Google Scholar

3a 10.1055/s-1999-2662, W. Schade, H.-U. Reissig. Synlett 632 (1999); review.Search in Google Scholar

3b see ref. [11].Search in Google Scholar

4 S. Hoff, L. Brandsma, J. F. Arens. Recl. Trav. Chim. Pays-Bas87, 916 (1968).10.1002/recl.19680871011Search in Google Scholar

5 10.1016/S0040-4039(01)94481-8, J. C. Clinet, G. Linstrumelle. Tetrahedron Lett. 1137 (1978).Search in Google Scholar

6a S. Hoff, L. Brandsma, J. F. Arens. Recl. Trav. Chim. Pays-Bas88, 609 (1969).10.1002/recl.19690880513Search in Google Scholar

6b 10.1021/jo00080a013, S. Hormuth, H.-U. Reissig. J. Org. Chem.59, 67 (1994).Search in Google Scholar

7a 10.1002/ange.200604078, M. Brasholz, H.-U. Reissig. Angew. Chem.119, 1659 (2007).Search in Google Scholar

7b 10.1002/anie.200604078, M. Brasholz, H.-U. Reissig. Angew. Chem., Int. Ed.46, 1634 (2007).Search in Google Scholar PubMed

8 10.1002/ejoc.200400173, O. Flögel, H.-U. Reissig. Eur. J. Org. Chem. 2797 (2004).Search in Google Scholar

9 10.1002/ejoc.200900450, M. Brasholz, H.-U. Reissig. Eur. J. Org. Chem. 3595 (2009).Search in Google Scholar

10 10.1055/s-1999-2966, M. Okala Amombo, A. Hausherr, H.-U. Reissig. Synlett 1871 (1999).Search in Google Scholar

11 O. Flögel, H.-U. Reissig. Synlett 895 (2004).Search in Google Scholar

12a 10.1002/chem.200390160, O. Flögel, M. G. Okala Amombo, H.-U. Reissig, G. Zahn, I. Brüdgam, H. Hartl. Chem.—Eur. J.9, 1405 (2003).Search in Google Scholar PubMed

12b 10.1002/hlca.200590143, S. Kaden, M. Brockmann, H.-U. Reissig. Helv. Chim. Acta88, 1826 (2005).Search in Google Scholar

12c M. A. Chowdhury, H.-U. Reissig. Synlett 2383 (2006).10.1055/s-2006-949622Search in Google Scholar

13 10.1021/ol061538y, S. Kaden, H.-U. Reissig. Org. Lett.8, 4763 (2006).Search in Google Scholar PubMed

14 10.1002/chem.200400322, O. Flögel, J. Dash, I. Brüdgam, H. Hartl, H.-U. Reissig. Chem.—Eur. J.10, 4283 (2004).Search in Google Scholar PubMed

15 10.1021/ol702468s, J. Dash, T. Lechel, H.-U. Reissig. Org. Lett.9, 5541 (2007).Search in Google Scholar PubMed

16 10.1002/adsc.200800789, C. Eidamshaus, H.-U. Reissig. Adv. Synth. Catal.351, 1162 (2009).Search in Google Scholar

17 10.1002/ejoc.200800398, T. Lechel, J. Dash, I. Brüdgam, H.-U. Reissig. Eur. J. Org. Chem. 3647 (2008).Search in Google Scholar

18 10.1002/chem.200900939, J. Dash, H.-U. Reissig. Chem.—Eur. J.15, 6811 (2009).Search in Google Scholar PubMed

19 10.1002/chem.200900386, T. Lechel, D. Lentz, H.-U. Reissig. Chem.—Eur. J.15, 5432 (2009).Search in Google Scholar PubMed

20 T. Lechel, S. Möhl, H.-U. Reissig. Synlett 1059 (2009).10.1055/s-0028-1088220Search in Google Scholar

Online erschienen: 2010-5-30
Erschienen im Druck: 2010-5-31

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