14997-05-8

Usage

Uses

Used in Organic Synthesis:
3-Pyridinecarboxylic acid, 1,4,5,6-tetrahydro-, methylester (9CI) is used as a reagent in organic synthesis for the production of various compounds. Its versatile chemical properties and reactivity contribute to its wide application in this field.
Used in Pharmaceutical Development:
3-Pyridinecarboxylicacid,1,4,5,6-tetrahydro-,methylester(9CI) serves as a building block in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs. Its potential biological activities and pharmacological uses make it an important compound in medicinal chemistry and drug discovery.
Used in Agrochemical Synthesis:
3-Pyridinecarboxylic acid, 1,4,5,6-tetrahydro-, methylester (9CI) is also utilized in the synthesis of agrochemicals, contributing to the development of effective and innovative products for agricultural applications.

Upstream product

• 304850-59-7 ethyl methyl piperidine-3,3-dicarboxylate 
• 1624302-00-6 1-tert-butyl 3-ethyl 3-methyl piperidine-1,3,3-tricarboxylate 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 59-67-6 nicotinic acid 

Downstream Products

• 126225-89-6 1-(2-bromobenzyl)-3-methoxycarbonyl-1,4,5,6-tetrahydropyridine 
• 111975-29-2 rel-(8R,8aS)-8-hydroxymethylperhydroindolizine 

Relevant academic research and scientific papers

Synthesis of aspidodispermine via pericyclic framework reconstruction

A divergent approach to the pyrroloquinoline scaffold as present in the class of Aspidosperma alkaloids was developed. As a case study, abundant and renewable nicotinic acid was transformed via pericyclic framework reconstruction into aspidodispermine, a unique member of pyrroloquinoline alkaloids. The sequence comprises a [2 + 2]-photocycloaddition, a Ramberg-B?cklund contraction, and a strain-promoted formal electrocyclic rearrangement of a bicyclo[2.2.0]hexene and is potentially extendable to pyrroloindole scaffolds as present in the ibophyllidine alkaloids.

Expedited Synthesis of Matrine Analogues through an Oxidative Cascade Addition/Double-Cyclization Radical Process

The addition of a nicotinate–xanthate derivative to N-allylindoles and N-allylpyrroles resulted in polycyclic heterocycle-fused pyridonaphthyridines through a tandem radical intermolecular/intramolecular oxidative addition reaction sequence that created three new C–C bonds and two new rings in a single event. Such polyheterocycles showcase the matrine alkaloid framework and are similar to indole–monoterpenoid natural products.

Towards a new synthetic entry into the Iboga-alkaloid family

A novel retrosynthetic concept is presented that, in principle, allows access to many hitherto not accessible representatives of the Iboga-alkaloid family. The flexibility required by this approach is provided through a highly convergent assembly of the target, which allows for a control over the substitution pattern of the indole sub-system, as well as over the relative configuration of the aliphatic core of these alkaloids. The key step for the construction of the latter consists in an intramolecular nitrone-olehn 1,3-dipolar cycloaddition reaction of 26 to yield the crucial tricyclic isoxazolidine derivative 28.