Kondrat'eva pyridine synthesis

The Kondrat'eva pyridine synthesis , named after GY Kondrat'eva , is a name reaction from the field of organic chemistry and was first described in 1957. The Kondrat'eva pyridine synthesis enables the preparation of pyridine derivatives from oxazole and a substituted alkene (also called dienophile ).

Overview reaction

Oxazole reacts with a dienophile with elimination of water to form pyridine . The reaction is an example of a Diels-Alder reaction . The newly made ties are marked in blue :

Reaction mechanism

A plausible reaction mechanism was formulated by Zerong Wang. Accordingly, the oxazole 1 reacts with the dienophile 2 to form the cycle 3 . The electron rearrangement leads to the conversion to a simple ring system. The pyridine derivative 4 is then formed with elimination of water and aromatization .

Individual evidence

^ ^A ^b Zerong Wang: Comprehensive Organic Name Reactions and Reagents. Wiley, 2009, ISBN 978-0-471-70450-8 , pp. 1668-1671.
↑ Jeremy I. Levin, Steven M. Weinreb: Synthesis of eupolauramine via an intramolecular Kondrat'eva pyridine synthesis. In: J. Org. Chem. 49, 1984, pp. 4325-4332, doi: 10.1021 / jo00197a001 .

[wang-1] A ^b Zerong Wang: Comprehensive Organic Name Reactions and Reagents. Wiley, 2009, ISBN 978-0-471-70450-8 , pp. 1668-1671.

[2] Jeremy I. Levin, Steven M. Weinreb: Synthesis of eupolauramine via an intramolecular Kondrat'eva pyridine synthesis. In: J. Org. Chem. 49, 1984, pp. 4325-4332, doi: 10.1021 / jo00197a001 .