14924-93-7

Upstream product

• 100-52-7 benzaldehyde 
• 123-38-6 propionaldehyde 
• 101-39-3 2-methyl-3-phenyl-2-propenal 
• 2450-71-7 Propargylamine 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 83463-05-2 1,5-Di-furan-2-yl-2,4-dimethyl-3-phenyl-pentane-1,5-dione 
• 83463-10-9 2,6-Di-furan-2-yl-3,5-dimethyl-4-phenyl-pyridine 
• 83463-01-8 (E)-1-(furan-2-yl)-2-methyl-3-phenylprop-2-en-1-one 
• 83463-14-3 3,5-Dimethyl-4-phenyl-pyridine-2,6-dicarboxylic acid 

Relevant academic research and scientific papers

Facile Synthesis of Pyridines from Propargyl Amines: Concise Total Synthesis of Suaveoline Alkaloids

A general and efficient protocol was developed for the synthesis of polysubstituted pyridines from propargyl amines and unsaturated carbonyl compounds through a tandem condensation/alkyne isomerization/6π 3-azatriene electrocyclization sequence. This process was found to be applicable to a wide range of readily available substrates (30 examples, up to 95 % yield) and could be readily performed on a preparative (20 g) scale. By taking advantage of this method for late-stage pyridine incorporation, we successfully completed the collective total synthesis of suveoline, norsuveoline, and macrophylline.

NOVEL METHODS FOR PREPARATION OF SUBSTITUTED PYRIDINES AND RELATED NOVEL COMPOUNDS

The present invention relates to novel methods of preparation of substituted pyridines and the compounds produced therefrom. In particular, the present invention provides efficient methods for the construction of diversely substituted pyridines, with varying substitution patterns under simple and metal-free conditions with high atom- and pot-economy and excellent functional group tolerance, and which are useful for the synthesis of natural products.

A simple, tandem approach to the construction of pyridine derivatives under metal-free conditions: A one-step synthesis of the monoterpene natural product, (-)-actinidine

A simple and modular one-step synthesis of diversely substituted pyridines from readily available α,β-unsaturated carbonyl compounds and propargylic amines has been developed. The present protocol has a broad substrate scope and allows access to multi-substituted pyridines with select control of the substitution pattern under mild and metal-free conditions. The reaction involves imine formation followed by concomitant cyclization through an allenyl intermediate to afford pyridines in excellent yields, with water as the sole by-product. This mild strategy is also suitable for functionalization of natural products or other advanced intermediates having α,β-unsaturated carbonyl functionality. The utility of the present protocol was showcased with the synthesis of the monoterpene alkaloid, (-)-actinidine, an ant-associated iridoid.

Quick Access to Pyridines through 6π-3-Azatriene Electrocyclization: Concise Total Synthesis of Suaveoline Alkaloids

Pyridine is a prevalent structural heterocyclic motifs in natural products, pharmaceuticals, and advanced materials. Several different methodologies have been developed for the synthesis of these kinds of molecules. However, a sustainable and efficient procedure for the synthesis of pyridines is still highly desirable. In this Synpacts article, we highlight our recent approach to the construction of highly substituted pyridines though a tandem condensation/alkyne isomerization/6π-3-azatriene electrocyclization sequence. The present protocol was used to synthesize a series of polysubstituted pyridines (30 examples) in moderate to good yields. The process also permitted the development of a concise strategy for collective total syntheses of suaveoline, norsuaveoline, and macrophylline.

SYNTHESIS OF ALKYL-SUBSTITUTED ARYLPYRIDINES IN THE VAPOR PHASE BY THE CHICHIBABIN METHOD

An industrial cadmium calcium phosphate catalyst was used in the syntheses of pyridine bases in the vapor phase by the Chichibabin method (condensation of carbonyl compounds with ammonia).Alkyl-substituted arylpyridines with the aryl radical at C2, C3, or C4 are formed during the condensation of aromatic aldehydes and ammonia with saturated and unsaturated aldehydes and also with methyl alkyl ketones.