Hantzsch pyridine synthesis

Hantzsch pyridine synthesis

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. [cite journal
title = Condensationprodukte aus Aldehydammoniak und Ketoniartigen Verbindungen
author = Hantzsch, A.
journal = Chemische Berichte
volume = 14
issue =
pages = 1637–1638
year = 1881
doi = 10.1002/cber.18810140214] The initial reaction product is a dihydropyridine which can be oxidized in a subsequent step to a pyridine. The driving force for this second reaction step is aromatization.

A 1,4-dihydropyridine dicarboxylate is also called a 1,4-DHP compound or a Hantzsch compound. These compounds are an important class of calcium channel blockers 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 or potassium permanganate in a one-pot synthesis.cite journal
title = One-Pot Synthesis and Aromatization of 1,4-Dihydropyridines in Refluxing Water
author = Jing-Jing Xia, Guan-Wu Wang
journal = Synthesis
volume = 2005
issue =
pages = 2379–2383
year = 2005
url = http://www.thieme-connect.com/ejournals/abstract/synthesis/doi/10.1055/s-2005-870022
doi = 10.1055/s-2005-870022
format = abstract]

The Hantzsch dihydropyridine synthesis is found to benefit from microwave chemistry. [cite journal
title = Synthesis and Aromatization of Hantzsch 1,4-Dihydropyridines under Microwave Irradiation. An Overview
author = Jean Jacques Vanden Eynde, Annie Mayence
journal = Molecules
volume = 8
issue =
pages =
year = 2003
url = http://www.mdpi.org/molecules/papers/80400381.pdf]

Knoevenagel-Fries modification

The Knoevenagel-Fries modification allows for the synthesis of unsymmetrical pyridine compounds [Synthesen in der Pyridinreihe. Ueber eine Erweiterung der Hantzsch'schen Dihydropyridinsynthese Berichte der deutschen chemischen Gesellschaft 1898 (p 761-767) E. Knoevenagel, A. Fries DOI|10.1002/cber.189803101157] .

References


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать курсовую

Look at other dictionaries:

  • Chichibabin pyridine synthesis — Not to be confused with Chichibabin reaction. The Chichibabin pyridine synthesis (pronounced (chē ) chē bā bēn) is a method for synthesizing pyridine rings. In its general form, the reaction can can be described as a condensation reaction of… …   Wikipedia

  • Pyridine — Pyridine …   Wikipedia

  • Pyridine — Structures de la pyridine Général Nom IUPAC Azine …   Wikipédia en Français

  • Arthur Rudolf Hantzsch — Infobox Scientist name = Arthur Rudolf Hantzsch image width = caption = birth date = 7 March, 1857 birth place = Dresden, Germany residence = Germany, Switzerland nationality = German death date = death date and age|1935|3|14|1857|3|7 death place …   Wikipedia

  • List of organic reactions — Well known reactions and reagents in organic chemistry include Contents: A B C D E F G H I J K L M N O P Q R S T U V W X Y Z    See also   Ext …   Wikipedia

  • Knoevenagel condensation — The Knoevenagel condensation reaction is an organic reaction named after Emil Knoevenagel. It is a modification of the Aldol condensation[1][2]. A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl… …   Wikipedia

  • Multi-component reaction — In chemistry, a multi component reaction (or MCR), sometimes referred to as a Multi component Assembly Process (or MCAP), is a chemical reaction where three or more compounds react to form a single product. [1] By definition, multicomponent… …   Wikipedia

  • Síntesis de piridina de Chichibabin — La Síntesis de piridina de Chichibabin es un método para sintetizar anillos de piridina. En su forma general, la reacción puede ser descripta como una reacción de condensación entre aldehídos, cetonas o compuestos Carbonilos α,β Insaturados o… …   Wikipedia Español

  • Thiazole — Chembox new ImageFile = Thiazole numbering.png ImageFile1 = Thiazole3d.png ImageSize = 100px IUPACName = OtherNames = Section1 = Chembox Identifiers CASNo = 288 47 1 PubChem = SMILES = N1=CSC=C1 Section2 = Chembox Properties Formula = MolarMass …   Wikipedia

  • 110-86-1 — Pyridine Pyridine Structures de la pyridine Général Nom IUPAC Azine …   Wikipédia en Français

Share the article and excerpts

Direct link
… Do a right-click on the link above
and select “Copy Link”