Schmidt Rearrangement Organic Chemistry M.Pharmacy 1st Semester 2022 (2021-2022) Previous Year's Question Papers/Notes Download - HK Technical PGIMS

TABLE OF CONTENTS

 INTRODUCTION
 MECHANISM
 APPLICATIONS
 REFERENCES

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INTRODUCTION

 The Schmidt reaction is the reaction of hydrazoic
acid or an alkyl azide with a carbonyl compound,
alkene, or alcohol, often in the presence of a
Bronsted or Lewis acid. The product is an amine,
imine, or amide, with the expulsion of nitrogen.

 The history of this reaction goes back to 1924 when
German chemist Karl Friedrich Schmidt reported it.

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COMMON REACTION
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Mechanism of Schmidt Reaction

 The Schmidt reaction is used to get an amide and
an amine by reacting hydrazoic acid to ketone and
carboxylic acid, respectively.

Synthetic applications

 The Schmidt reaction has been applied to the synthesis of disubstituted
amino acids. After asymmetric alkylation of a β-ketoester, treatment
with trifluoroacetic acid (TFA) and sodium azide yields the N-acetyl
amino ester, which may be converted to the corresponding amino acid
through functional group manipulations

The Schmidt reaction has also been applied extensively to access crowded or
otherwise difficult amines and amides in alkaloid natural products. Efforts
toward the homoerythrina spirocyclic ring system contain a nice application
of the intramolecular Schmidt reaction of alkyl azides.