Knorr pyrrole synthesis

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The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3).[1][2][3] The method involves the reaction of an α-amino-ketone (1) and a compound containing a methylene group α- to (bonded to the next carbon to) a carbonyl group (2).[4]

The Knorr pyrrole synthesis

[edit] Method

The mechanism requires zinc and acetic acid as catalysts. It will proceed at room temperature. Because α-amino-ketones self-condense very easily, they must be prepared in situ. The usual way of doing this is from the relevant oxime.[5][6]

[edit] References

  1. ↑  Knorr, L. Ber. 1884, 17, 1635.
  2. ↑  Knorr, L. Ann. 1886, 236, 290.
  3. ↑  Knorr, L.; Lange, H. Ber. 1902, 35, 2998.
  4. ↑  Corwin, A. H. Heterocyclic Compounds 1950, 1, 287. (Review)
  5. ↑  Fischer, H. Organic Syntheses, Coll. Vol. 2, p.202 (1943); Vol. 15, p.17 (1935). (Article)
  6. ↑  Fischer, H. Organic Syntheses, Coll. Vol. 3, p.513 (1955); Vol. 21, p.67 (1941). (Article)

[edit] See also

  • Hantzsch pyrrole synthesis
  • Paal-Knorr pyrrole synthesis


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