Magnesium Methoxide-Assisted Synthesis of 2,4,6-Triaryl Pyridines

A new three-component reaction of chalcones, ketones, and ammonia assisted by magnesium methoxide is described. The corresponding 2,4,6-triaryl pyridines (Kröhnke pyridines) are formed in fair to good yields (34–76%) within 3 h. The method also provides a facile way to synthesize 2(6)-difluoromethyl pyridines via an interesting mechanism.     

Green Method for the Synthesis of Benzo[f]pyrimido[4,5-b]quinoline Derivatives Catalyzed by Iodine in Aqueous Media

A convenient one-pot synthesis of benzo[f]pyrimido[4,5-b]quinoline derivatives is described via three-component reaction of benzaldehydes, naphthalen-2-amine, and barbituric acid at room temperature in aqueous media catalyzed by iodine. Compared with other methods, this three-component reaction used a green solvent, gave good yields, and was operationally simple.     

Three-Component,Four-Molecule,Ru-Catalyzed Cascade Reactions of Indoles and Alkyl Bromides with Sodium Nitrite

Abstract

An operationally simple domino approach for the ruthenium-catalyzed synthesis of (E)-2,3′-bi(3H-indol)-3-one O-alkyl oximes by the region- and stereoselective three-component, four-molecule reactions of indoles with sodium nitrite and alkyl bromides under mild reaction condition in dimethylformamide is described. Remarkably, multiple bonds including C?C, C=N, and C?O bonds were conveniently formed in one pot. The reaction is tolerant to air and is atom economical, in accordance with the concept of modern green chemistry.     

Preferential Reactivity of Pyridylmagnesiumchloride with N,N-Dialkyl Arylamides over Carbonitriles: Synthesis of 2-(Aroyl) Pyridines

Reaction of 2-pyridylmagnesium chlorides with N,N-dialkyl arylamides afford exclusively 2-(aroyl) pyridines in high yields and purity without the formation of any tertiary alcohol. This method employs easily available raw materials and avoids the use of hazardous lithium reagents and cryogenic conditions. Further, preferential reactivity of this Grignard reagent with N,N-dialkyl arylamides over its carbonitrile counterparts offers a variety of 2-(aroyl) pyridines including the ones containing carbonitrile groups on the aryl ring.     

Expeditious Approach to Coumarins via Pechmann Reaction Catalyzed by Molecular Iodine or AgOTf

An efficient and facile route for the synthesis of coumarins via the Pechmann reaction catalyzed by molecular iodine or AgOTf was described.     

Reactions of Neomycin B under Mitsunobu Conditions: A Correction of the Literature

Reaction of N‐Boc neomycin with triphenylphosphine and diissopropyl azodicarboxylate in either toluene or THF results in an epoxide in ring IV, not an aziridine or azetidine as previously reported.     

Lanthanide Triflate Catalyzed One-Pot Synthesis of Dihydropyrimidin-2(1H)-thiones by a Three-Component of 1,3-Dicarbonyl Compounds,Aldehydes, and Thiourea Using a Solvent-Free Biginelli Condensation

Abstract

Novel one-pot Biginelli-type reaction has been developed. Aromatic and aliphatic aldehydes with β-dicarbonyl compounds and thiourea in the presence of catalytic amount 5 mol% of Yb(OTf)₃ at 100° C for 60–90 min under solvent-free conditions proceeded smoothly to afford corresponding dihydropyrimidin-thiones. The yields of the classical Biginelli reaction can be increased from 20–50% to 81–91% while the reaction time was shortened from 18–48 h to 60–90 min. In addition the catalyst can be easily recovered and reused.     

A Photochemical Approach to a Potential Precursor of the Bicyclo [6.4.0] Dodecane Ring System of Taxane Diterpenes

The intermolecular [2+2] photocycloaddition of dimedone 6 and 1-acetoxy-2-methyl-5-dioxolan-1-hexene 7 followed by alkaline treatment, gave the 1,5,5,11-tetramethyl-7-dioxolan bicyclo [4,3,2]-4-decen-2,3-dione 12, and the 1,5,5-trimethyl-3-hydroxy-7-dioxolan bicyclo [5,4,1] dodecan-2,11-dione 13.     

Organocatalytic Conjugate Addition of Azide Ion to α,β‐Unsaturated Aldehydes

An efficient and simple amine‐catatalyzed azide conjugate addition to α,β‐unsaturated aldehydes has been developed. In the presence of a catalytic amount of tertiary amine with a 1:1 mixture of NaN₃ and 37% HCl in CH₂Cl₂, α,β‐unsaturated aldehydes provided β‐azido aldehydes, which could be transformed into 1,3‐amino alcohols.     

Scope and Applicability of an Expedient Synthesis Leading to Polysubstituted 3‐(Carboxyphenyl)pyrroles

A convenient three‐step route toward a functionalized pyrrole building block for novel anti‐inflammatory agents is reported. In contrast to previous strategies, the present approach focuses on inexpensive starting materials and application on a multigram scale. A high degree of functional diversity is demonstrated in various derivatives, and the scope and limitations of this route are discussed. Complementary to the described tetrasubstituted pyrroles, a novel ring‐closure protocol based on the Feist–Benary condensation affords trisubstituted analogues.