Abstract
Reaction between 1,4-diketones and primary amines (or ammonia) to give pyrroles. A variation of the Knorr pyrazole synthesis.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
-
1.
(a) Paal, C. Ber. 1885, 18, 367-371. (b) Paal, C. Ber. 1885, 18, 2251-2254. (c) Knorr, L. Ber. 1885, 18, 299-311.
-
2.
Corwin, A. H. Heterocyclic Compounds Vol. 1, Wiley, NY, 1950; Chapter 6. (Review).
-
3.
Jones, R. A.; Bean, G. P. The Chemistry of Pyrroles, Academic Press, London, 1977, pp 51-57, 74-79. (Review).
-
4.
(a) Brower, P. L.; Butler, D. E.; Deering, C. F.; Le, T. V.; Millar, A.; Nanninga, T. N.; Roth, B. D. Tetrahedron Lett. 1992, 33, 2279-2282. (b) Baumann, K. L.; Butler, D. E.; Deering, C. F.; Mennen, K. E.; Millar, A.; Nanninga, T. N.; Palmer, C. W.; Roth, B. D. Tetrahedron Lett. 1992, 33, 2279, 2283-2284.
-
5.
de Laszlo, S. E.; Visco, D.; et al. Bioorg. Med. Chem. Lett. 1998, 8, 2689-2694.
-
6.
Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300.
-
7.
Quiclet-Sire, B.; Quintero, L.; Sanchez-Jimenez, G.; Zard, Z. Synlett 2003, 75-78.
-
8.
Gribble, G. W. Knorr and Paal-Knorr Pyrrole Syntheses. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Corey, E. J., Eds, Wiley: Hoboken, NJ, 2005, 77-88. (Review).
-
9.
Salamone, S. G.; Dudley, G. B. Org. Lett. 2005, 7, 4443-4445.
-
10.
Fu, L.; Gribble, G. W. Tetrahedron Lett. 2008, 49, 7352-7354.
-
11.
Trushkov, I. V.; Nevolina, T. A. Tetrahedron Lett. 2013, 54, 3974-3976.
-
12.
Wiest, J. M.; Bach, T. J. Org. Chem. 2016, 81, 6149-6156.
-
13.
Liu, Y.; Lindsey, J. S. J. Org. Chem. 2016, 81, 11882-11897.
-
14.
Xu, B.; Li, G.; Li, J.; Shi, Y. Org. Lett. 2016, 18, 2028-2031.
-
15.
Chen, J.-J.; Xu, Y.-C.; Gan, Z.-L.; Peng, X.; Yi, X.-Y. Eur. J. Inorg. Chem. 2019, 1733-1739.
-
16.
Zelina, E. Y.; Nevolina, T. A.; Sorotskaja, L. N.; Skvortsov, D. A.; Trushkov, I. V.; Uchuskin, M. G. Tetrahedron Lett. 2020, 61, 151532.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2021 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Li, J.J. (2021). Paal–Knorr Pyrrole Synthesis. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-030-50865-4_113
Download citation
DOI: https://doi.org/10.1007/978-3-030-50865-4_113
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-50864-7
Online ISBN: 978-3-030-50865-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)