Pinner triazine synthesis

Last updated May 02, 2019

The Pinner triazine synthesis describes the preparation of 2-hydroxyl-4,6-diaryl-s-triazines by reaction of aryl amidines and phosgene. This reaction may be extended to halogenated aliphatic amidines. [1] [2] [3]

A triazine is class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C₃H₃N₃. They exist in three isomeric forms, 1,3,5-triazines being common.

In the context of organic molecules, aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as a placeholder for the aryl group in chemical structure diagrams.

Phosgene is the chemical compound with the formula COCl₂. A colorless gas, in low concentrations its odor resembles freshly cut hay or grass. Phosgene is a valued industrial building block, especially for the production of urethanes and polycarbonate plastics. However, it is very poisonous and was used as a chemical weapon during World War I where it was responsible for 85,000 deaths. In addition to its industrial production, small amounts occur from the breakdown and the combustion of organochlorine compounds.

This reaction was first reported by Adolf Pinner in 1890 [4]

Adolf Pinner was a German chemist.

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The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt ; this is sometimes referred to as a Pinner salt. The reaction is named after Adolf Pinner, who first described it in 1877. Pinner salts are themselves reactive and undergo additional nucleophilic additions to give various useful products:

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1,3,5-triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)₃. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine and its derivatives are useful in a variety of applications.

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The Bamberger triazine synthesis in organic chemistry is a classic organic synthesis of a triazine first reported by Eugen Bamberger in 1892.

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Ammeline (4,6-diamino-2-hydroxy-1,3,5-triazine) is a triazine derivative. It is the hydrolysis product of melamine.

In enzymology, a hydroxydechloroatrazine ethylaminohydrolase (EC 3.5.99.3) is an enzyme that catalyzes the chemical reaction

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Carboximidates are organic compounds, which can be thought of as esters formed between a carboximidic acid and an alcohol, with the general formula R-C(=NR')OR".

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The Boger pyridine synthesis is a cycloaddition approach to the formation of pyridines named after its inventor Dale L. Boger, who first reported it in 1981. The reaction is a form of inverse-electron demand Diels-Alder reaction in which an enamine reacts with a 1,2,4-triazine to form the pyridine nucleus. The reaction is especially useful for accessing pyridines that would be difficult or impossible to access via other methods and has been used in the total synthesis of several complicated natural products.

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References

↑ H. Schröder, C. Grundmann, J. Am. Chem. Soc. 78, 2447 (1956)
↑ E. M. Smolin, L. Rapoport, The Chemistry of Heterocyclic Compounds, A. Weissberger, Ed., s-Triazines and Derivatives (Interscience, NY, 1959) p186
↑ Merck Index 14th Ed.
↑ A. Pinner, Chemische Berichte., 23, 2919 (1890)

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[1] H. Schröder, C. Grundmann, J. Am. Chem. Soc. 78, 2447 (1956)

[2] E. M. Smolin, L. Rapoport, The Chemistry of Heterocyclic Compounds, A. Weissberger, Ed., s-Triazines and Derivatives (Interscience, NY, 1959) p186

[3] Merck Index 14th Ed.

[4] A. Pinner, Chemische Berichte., 23, 2919 (1890)