2052-92-8

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 12, p. 709, 1975 DOI: 10.1002/jhet.5570120419

InChI:InChI=1/C12H11N/c1-10-9-13-8-7-12(10)11-5-3-2-4-6-11/h2-9H,1H3

Upstream product

• 13515-63-4 1,3-dimethyl-4-phenyl-1,2,5,6-tetrahydropyridine 
• 108-99-6 3-Methylpyridine 
• 98-88-4 benzoyl chloride 
• 46268-56-8 4-phenyl-3-pyridinecarbaldehyde 
• 114655-48-0 (E)-2-methyl-N-((E)-3-phenylallylidene)propan-2-amine 
• 123-38-6 propionaldehyde 
• 106-51-4 p-benzoquinone 
• 14371-10-9 (E)-3-phenylpropenal 
• 2450-71-7 Propargylamine 
• 15430-52-1 prop-2-yn-1-amine hydrochloride 
• 71-43-2 benzene 
• 104-55-2 3-phenyl-propenal 
• 591-50-4 iodobenzene 
• 4733-71-5 1,3-dimethyl-4-phenyl-piperidin-4-ol 

Downstream Products

• 113120-10-8 3-methyl-4-(4-nitrophenyl)pyridine 
• 95969-41-8 1,5-dimethyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide 
• 13515-63-4 1,3-dimethyl-4-phenyl-1,2,5,6-tetrahydropyridine 
• 95968-88-0 1,3-dimethyl-4-phenylpyridinium iodide 

Relevant academic research and scientific papers

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.

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.

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.

Pd(II)-Catalyzed C3-Selective Arylation of Pyridine with (Hetero)arenes

Palladium catalyzed, nondirected C3-selective arylation of pyridines with arenes and heteroarenes in the presence of 1,10-phenanthroline as the ligand has been developed. The optimized conditions allow for a highly C3-selective arylation of pyridines, affording various 3,3′-bipyridines and 3-arylpyridines. (Chemical Equation Presented).

Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

AMVN-initiated expedient synthesis of biaryls by the coupling reaction of unactivated arenes and heteroarenes with aryl iodides

The role of radical initiators AMVN and AIBN has been studied in the potassium tert-butoxide mediated biaryl coupling reaction of aryl iodides with unactivated arenes. Radical initiator AMVN promoted carbon-carbon bond formation expeditiously from aryl iodide having various groups such as amino, methoxy, fluoro, methyl, and trifluoromethyl and arenes in the presence of potassium tert-butoxide (4 equiv.) at 110 °C in 2-5 h. Substituted arenes such as toluene, xylene, anisole, and fluorobenzene also proceeded to form biaryls under AMVN-initiated reaction conditions. Moreover naphthalene, pyridine, pyrimidine, and pyridazine also coupled with aryl iodides and produced biaryls in 41-82% yields. It seems that AMVN initiates the formation of the aryl radical, which enters the radical chain reaction. The generated aryl radical may combine with the arene leading to a biaryl radical, which upon protonation gives the biphenyl radical anion and tert-butanol. The biphenyl radical anion finally reacts with the aryl iodide generating the aryl radical and thus completes the radical chain reaction with concomitant release of biphenyl.

A Pd(II)-catalyzed ring-expansion reaction of cyclic 2-azidoalcohol derivatives: Synthesis of azaheterocycles

(Chemical Equation Presented) A Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via an unprecedented C-C bond cleavage-C-N bond formation sequence, providing substituted azaheterocycles.

Novel CDK inhibition profiles of structurally varied 1-aza-9-oxafluorenes

A series of 1-aza-9-oxafluorenes with functionally varied 3-substituents have been prepared from N-phenoxycarbonyl-4-phenyl-1,4-dihydropyridines and p-benzoquinone and biologically evaluated as inhibitors of various cyclin-dependant kinases. The absence o