Propose a mechanism for the reaction of glucosamine with acetylacetone to form product containing the pyrrole ring. Hint: The likely first step involves attack of the nucleophilic amino group of glucosamine on one of the carbonyl carbons of acetylacetone and leads to formation of an aminoalcohol. This can dehydrate to form a α,β unsaturated carbonyl compound. The alkene can then react with the aldehyde to form a ring structure.
Propose a mechanism for the reaction of glucosamine with acetylacetone to form product containing the pyrrole ring. Hint: The likely first step involves attack of the nucleophilic amino group of glucosamine on one of the carbonyl carbons of acetylacetone and leads to formation of an aminoalcohol. This can dehydrate to form a α,β unsaturated carbonyl compound. The alkene can then react with the aldehyde to form a ring structure.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter17: Carboxylic Acids
Section: Chapter Questions
Problem 17.24P
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Propose a mechanism for the reaction of glucosamine with acetylacetone to form product containing the pyrrole ring.
Hint: The likely first step involves attack of the nucleophilic amino group of glucosamine on one of the carbonyl carbons of acetylacetone and leads to formation of an aminoalcohol. This can dehydrate to form a α,β unsaturated carbonyl compound. The
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