Hantzsch pyridine synthesis
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The Hantzsch pyridine synthesis or Hantzsch dihydropyridine synthesis is a multi-component organic reaction between an aldehyde such as formaldehyde, 2 equivalents of a β-keto ester such as ethyl acetoacetate and a nitrogen donor such as ammonium acetate or ammonia.[1][2] The initial reaction product is a dihydropyridine which can be oxidized in a subsequent step to a pyridine.[3] The driving force for this second reaction step is aromatization. This reaction was reported in 1881 by Arthur Rudolf Hantzsch.
Hantzsch pyridine synthesis | |
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Named after | Arthur Rudolf Hantzsch |
Reaction type | Ring forming reaction |
Identifiers | |
Organic Chemistry Portal | hantzsch-dihydropyridine-synthesis |
RSC ontology ID | RXNO:0000268 |
A 1,4-dihydropyridine dicarboxylate is also called a 1,4-DHP compound or a Hantzsch ester. These compounds are an important class of calcium channel blockers[2] and as such commercialized in for instance nifedipine, amlodipine or nimodipine.
The reaction has been demonstrated to proceed in water as reaction solvent and with direct aromatization by ferric chloride, manganese dioxide or potassium permanganate in a one-pot synthesis.[4]
The Hantzsch dihydropyridine synthesis has been effected by microwave chemistry.[5]