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Relevant academic research and scientific papers

Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines

Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing α-chlorodiazirines as thermal precursors to the corresponding chlorocarbenes, the traditional haloform-based protocol central to the parent Ciamician-Dennstedt rearrangement can be modified to directly afford 3-(hetero)arylpyridines and quinolines. Chlorodiazirines are conveniently prepared in a single step by oxidation of commercially available amidinium salts. Selectivity as a function of pyrrole substitution pattern was examined, and a predictive model based on steric effects is put forward, with DFT calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is further demonstrated through the preparation of quinolinophanes and the skeletal editing of pharmaceutically relevant pyrroles.

Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate

A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridinesvia t-BuOK/DMSO-promotedC-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of thein situgenerated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.

Lewis Acid-Promoted Ring-Contraction of 2,4,6,8-Tetrasubstituted 1,5-Diazacyclooctatetraenes to 2,4,6-Trisubstituted Pyridines

Ring-contraction of 2,4,6,8-tetrasubstituted 1,5-diazacyclooctatetraenes was highly efficiently promoted by Lewis acid such as TiCl4, affording 2,4,6-trisubstituted pyridines in excellent yields, along with release of a nitrile. A reaction mechanism involving a 6π electrocyclic ring-closing followed by a retro [2 + 2] cyclization of an 1-azetine moiety was supported by both experimental observations and density functional theory calculation.

Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines

A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.

Synthesis of multisubstituted pyridines

By utilizing amino allenes, aldehydes, and aryl iodides as readily available building blocks, a simple and modular synthesis of multisubstituted pyridines with flexible control over the substitution pattern has been achieved. The method employs a two-step

MOLECULAR POLARIZABILITY OF ORGANIC COMPOUNDS AND THEIR COMPLEXES. XLV. CONFORMATIONS OF SOME 2-ARYL-4-PHENYL-6-tert-BUTYLPYRIDINES IN DIOXANE SOLUTIONS

Conformations of a series of 2-aryl-4-phenyl-6-tert-butylpyridines in dioxane solution were determined by Kerr-effect and dipole-moment methods.The molecules of these compounds are acoplanar, and the aryl nuclei in position 2 of the heteroring deviate from the plane of the pyridine ring by an angle of 25-64 deg, which approximately corresponds to the conformations of biphenyl and its para-substituted derivatives.A nitro group located para in the ring in position 2 of the 2,4-diphenyl-6-tert-butylpyridine molecule reduces the acoplanarity of the 2-aryl substituent relative to the pyridine ring as a result of the mesomeric interaction of the 2-nitroaryl with the latter.

A Novel Formation of Phenyl-Substituted Pyridines by the Reaction of N-(Diphenylphosphinyl)-1-azaallyl Anions with α,β-Unsaturated Carbonyl Compounds. A New Synthetic Equivalent of Primary Vinylamines

The N-phosphinyl-1-azaallyl anions, which were derived from the corresponding imine or enamine reacted with α,β-unsaturated carbonyl compounds to afford phenyl-substituted pyridines along with 1-propanone and 1,5-pentanedione derivatives.A plausible mechanism involving a sequence of Michael addition and intramolecular aza-Horner-Wittig reaction is described, and the 1-azaallyl anions were found to behave as a synthetic equivalent of primary vinylamines.

The Synthesis and Reactions of Sterically Constrained Pyrylium and Pyridinium Salts

Efficient syntheses are developed for several pyrylium cations with substitution patterns more sterically demanding than 2,4,6-triphenyl and these are examined as reagents for the conversion of primary amino into a leaving group.The 2-mesityl-4,6-diphenyl derivative did not react smoothly with amines.The 2,6-di-t-butyl-4-phenyl-pyrylium cation gave the corresponding pyridinium derivatives, but they resisted nucleophilic attack. 2-t-Butyl-4,6-diphenylpyridinium cations suffer nucleophilic attack with about the same ease as the 2,4,6-triphenyl analogues.Dihydrobenzopyrylium (6) and tetrahydrodibenzoxanthylium cations (7) gave pyridinium cations which underwent much easier nucleophilic attack: thus they alkylate xanthate anion in ethanol solution and acetate anion in acetic acid.