Rh2(OAc)4-mediated diazo decomposition of δ-(N-Tosyl)amino-β-keto-α-diazo carbonyl compounds: A novel approach to pyrrole derivatives

Synlett

Volumn , Issue 11, 2002, Pages 1913-1915

  Deng, Guisheng ^a   Jiang, Nan ^a   Ma, Zhihua ^a   Wang, Jianbo ^a  

^a Peking University   (China)

Author keywords

Diazo compounds; Nucleophilic additions; Pyrroles; Rh(II) carbene; Ti(IV) enolate

Indexed keywords

AZO COMPOUND; CARBONYL DERIVATIVE; KETONE DERIVATIVE; PYRROLE DERIVATIVE; RHODIUM; TITANIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DECOMPOSITION; POLYMERIZATION; REACTION ANALYSIS;

EID: 0036431541     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34888     Document Type: Article

References (20)

1. Comprehensive Heterocyclic Chemistry, Vol. 2; Bird, C. W., Ed.; Pergamon Press: Oxford, 1996.
2. For recent examples of pyrrole syntheses based on Paal-Knorr reaction, see: (a) Hewton, C. E.; Kimber, M. C.; Taylor, D. K. Tetrahedron Lett. 2002, 43, 3199. (b) Takaya, H.; Kojima, S.; Murahashi, S.-I. Org. Lett. 2001, 3, 421. (c) Braun, R. U.; Zeitler, K.; Muller, T. J. J. Org. Lett. 2001, 3, 3297. (d) Surya Prakash Rao, H.; Jothilingam, S. Tetrahedron Lett. 2001, 42, 6595.
3. For recent examples of pyrrole syntheses based on Paal-Knorr reaction, see: (a) Hewton, C. E.; Kimber, M. C.; Taylor, D. K. Tetrahedron Lett. 2002, 43, 3199. (b) Takaya, H.; Kojima, S.; Murahashi, S.-I. Org. Lett. 2001, 3, 421. (c) Braun, R. U.; Zeitler, K.; Muller, T. J. J. Org. Lett. 2001, 3, 3297. (d) Surya Prakash Rao, H.; Jothilingam, S. Tetrahedron Lett. 2001, 42, 6595.
4. For recent examples of pyrrole syntheses based on Paal-Knorr reaction, see: (a) Hewton, C. E.; Kimber, M. C.; Taylor, D. K. Tetrahedron Lett. 2002, 43, 3199. (b) Takaya, H.; Kojima, S.; Murahashi, S.-I. Org. Lett. 2001, 3, 421. (c) Braun, R. U.; Zeitler, K.; Muller, T. J. J. Org. Lett. 2001, 3, 3297. (d) Surya Prakash Rao, H.; Jothilingam, S. Tetrahedron Lett. 2001, 42, 6595.
5. For recent examples of pyrrole syntheses based on Paal-Knorr reaction, see: (a) Hewton, C. E.; Kimber, M. C.; Taylor, D. K. Tetrahedron Lett. 2002, 43, 3199. (b) Takaya, H.; Kojima, S.; Murahashi, S.-I. Org. Lett. 2001, 3, 421. (c) Braun, R. U.; Zeitler, K.; Muller, T. J. J. Org. Lett. 2001, 3, 3297. (d) Surya Prakash Rao, H.; Jothilingam, S. Tetrahedron Lett. 2001, 42, 6595.
6. For recent examples of pyrrole syntheses that are not based on Paal-Knorr reaction, see: (a) Chen, N.; Lu, Y.; Gadamasetti, K.; Hurt, C. R.; Norman, M. H.; Fotsch, C. J. Org. Chem. 2000, 65, 2603. (b) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819. (c) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339. (d) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074. (e) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (f) Lagu, B.; Pan, M.: Wachter, M. P. Tetrahedron Left. 2001, 42, 6027.
7. For recent examples of pyrrole syntheses that are not based on Paal-Knorr reaction, see: (a) Chen, N.; Lu, Y.; Gadamasetti, K.; Hurt, C. R.; Norman, M. H.; Fotsch, C. J. Org. Chem. 2000, 65, 2603. (b) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819. (c) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339. (d) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074. (e) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (f) Lagu, B.; Pan, M.: Wachter, M. P. Tetrahedron Left. 2001, 42, 6027.
8. For recent examples of pyrrole syntheses that are not based on Paal-Knorr reaction, see: (a) Chen, N.; Lu, Y.; Gadamasetti, K.; Hurt, C. R.; Norman, M. H.; Fotsch, C. J. Org. Chem. 2000, 65, 2603. (b) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819. (c) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339. (d) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074. (e) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (f) Lagu, B.; Pan, M.: Wachter, M. P. Tetrahedron Left. 2001, 42, 6027.
9. For recent examples of pyrrole syntheses that are not based on Paal-Knorr reaction, see: (a) Chen, N.; Lu, Y.; Gadamasetti, K.; Hurt, C. R.; Norman, M. H.; Fotsch, C. J. Org. Chem. 2000, 65, 2603. (b) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819. (c) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339. (d) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074. (e) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (f) Lagu, B.; Pan, M.: Wachter, M. P. Tetrahedron Left. 2001, 42, 6027.
10. For recent examples of pyrrole syntheses that are not based on Paal-Knorr reaction, see: (a) Chen, N.; Lu, Y.; Gadamasetti, K.; Hurt, C. R.; Norman, M. H.; Fotsch, C. J. Org. Chem. 2000, 65, 2603. (b) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819. (c) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339. (d) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074. (e) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (f) Lagu, B.; Pan, M.: Wachter, M. P. Tetrahedron Left. 2001, 42, 6027.
11. For recent examples of pyrrole syntheses that are not based on Paal-Knorr reaction, see: (a) Chen, N.; Lu, Y.; Gadamasetti, K.; Hurt, C. R.; Norman, M. H.; Fotsch, C. J. Org. Chem. 2000, 65, 2603. (b) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819. (c) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339. (d) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074. (e) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (f) Lagu, B.; Pan, M.: Wachter, M. P. Tetrahedron Left. 2001, 42, 6027.
12. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley Interscience: New York, 1998.
13. (a) Calter, M. A.; Sugathapala, P. M.; Zhu, C. Tetrahedron Lett. 1997, 38, 3837.
14. (b) Calter, M. A.; Sugathapala, P. M. Tetrahedron Lett. 1998, 39, 8813.
15. (c) Calter, M. A.; Zhu, C. J. Org. Chem. 1999, 64, 1415.
16. 5S: C, 57.82; H, 5.09; N, 10.11. Found: C, 57.85; H, 5.09; N, 10.01.
17. For examples of intramolecular N-H bond insertion, see: (a) Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223. (b) Wang, J.; Hou, Y. J. Chem. Soc., Perkin Trans. 1 1999, 2277.
18. For examples of intramolecular N-H bond insertion, see: (a) Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223. (b) Wang, J.; Hou, Y. J. Chem. Soc., Perkin Trans. 1 1999, 2277.
19. General procedure for the diazo decomposition of 3 with catalyst. Abstract
20. p-Toluenesufinic acid was further converted to thiosulfonic ester, which is isolated and characterized.