93026-61-0

Upstream product

• 19823-75-7 2-(2-propynyl)cyclohexanone 
• 100-46-9 benzylamine 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 513-31-5 2-bromoallyl bromide 
• 290825-97-7 2-(3-trimethylsilyl-prop-2-ynyl)-cyclohexanone 
• 4471-09-4 N-benzylcyclohexylimine 
• 129286-74-4 (+/-)-N,N-dibenzylalaninal 
• 108-94-1 cyclohexanone 
• 53626-84-9 2-(2-bromo-2-propen-1-yl)cyclohexanone 
• 17392-07-3 2-(2-chloroprop-2-enyl)cyclohexanone 
• 86953-53-9 Benzyl-[2-(2-bromo-allyl)-cyclohex-(Z)-ylidene]-amine 

Relevant academic research and scientific papers

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

The bis-ortho-thioether 9,10-bis[(o-methylthio)phenyl]anthracene was synthesized as a syn-atropisomer, as revealed by X-ray diffraction. This alkylaryl thioether ligand (L) formed different macrocyclic complexes by coordination with silver(I) salts depending on the nature of the anion: M2L2 for AgOTf and AgOTFA, M6L4 for AgNO3. A discrete M2L complex was obtained in the presence of bulky PPh3AgOTf. These silver(I) complexes adopted similar structures in solution and in the solid state. As each sulfur atom in the ligand is prochiral, macrocycles L2M2 were obtained as mixtures of diastereoisomers, depending on the configurations of the sulfur atoms coordinated to silver cations. The X-ray structures of the two L2·(AgOTf)2 stereoisomers highlighted their different geometry. The catalytic activity of all silver(I) complexes was effective under homogeneous conditions in two tandem addition/cycloisomerization of alkynes using 0.5-1 mol % of catalytic loading.

Synthesis of pyrroles via copper-catalyzed coupling of amines with bromoenones

The CuI/N,N-dimethylglycine hydrochloride catalyzed reactions of amines with γ-bromo-substituted γ,δ-unsaturated ketones in the presence of K3PO4 and NH4OAc led to the formation of the corresponding polysubstituted pyrrole

Pyrrole synthesis catalyzed by AgOTf or cationic Au(I) complexes

Either silver trifluoromethanesulfonate or a mixture of gold(I) chloride, silver trifluoromethanesulfonate, and triphenylphosphine catalyze the formation of pyrroles from substituted β-alkynyl ketones and amines. The reactions proceed by using 5 mol % of catalyst with yields of isolated pyrroles ranging from 13% to 92%. Sixteen examples are used to compare the effectiveness of each catalyst.

One-pot synthesis of N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives

We describe the preliminary results of one-pot syntheses of various N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives from 2-(2-bromoallyl)cyclohexanone and the corresponding primary amines in good yields. Aliphatic amines were directly converted to tetrahydroindoles, whereas aromatic amines needed an extra base treatment step to complete the transformation.

A versatile synthesis of polysubstituted pyrroles

The aldol products formed by the reaction between α-(N-benzyl or N-Cbz)amino aldehydes and lithium enolates of various ketones, were subjected to hydrogenolysis to give polysubstituted pyrroles in good yields (50-91%). The scope and limitations of this me

Synthesis of functionalised furans and pyrroles through annulation reactions of 4-pentynones

A new approach to 4-pentynones through palladium-catalysed coupling reaction of the ready available 2-propynyl ketones with aryl iodides and/or vinyl triflates is proposed. Annulation reactions of both 2-propynyl ketones and 4-pentynones gave functionalised furans using potassium tert-butoxide in DMF and functionalised pyrroles in the presence of benzylamine or ammonia, respectively in good to high yields. The methodology has been extended to the preparation of 17β-hydroxyandrost-4-en[3,2-b](5-methyl)furan and to 17β- hydroxyandrost-4-en[3,2-b](1-benzyl-5-methyl)pyrrole. A different reaction pattern was observed when the 4-pentynones were treated with sodium methoxide in MeOH. The influence of the reaction medium on the outcome of the annulation reaction in the case of one 2-pentyn-1,6-dione (heteroannulation vs. carbocyclization) is also shown.

Sequential Addition/Elimination/Annulation Reactions of 4-Pentynones with Benzylamine and Ammonia

The sequential addition/elimination/cycloammination of 4-pentynones in the presence of benzylamine or ammonia produces 1,2,3,-5-substituted and 2,3,5-substituted pyrroles and fused pyrrole sytems, respectively in good to high yields. The methodology has been extended to the preparation of the 17β-hydroxyandrost-4-ene[3,2-b](1-benzyl-5-methyl)pyrrole.