343823-36-9

Upstream product

• 58327-36-9 α-Bromo-α-(4-methoxyphenyl)acetonitrile 
• 3585-93-1 N-(4-methoxybenzylidene)aniline oxide 
• 123-11-5 4-methoxy-benzaldehyde 
• 773837-37-9 sodium cyanide 
• 6443-74-9 p-methoxy-α-p-methoxyphenylcinnamonitrile 
• 104-47-2 p-methoxybenzylnitrile 

Downstream Products

• 2048-10-4 3,4-bis (4-methoxyphenyl)-1H-pyrrole 
• 170238-94-5 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 170238-96-7 methyl 3,4-bis(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate 

Relevant academic research and scientific papers

A Paal-Knorr approach to 3,4-diaryl-substituted pyrroles: Facile synthesis of lamellarins O and Q

A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.

ALLYLATION AND OXIDATION REACTIONS PROMOTED BY COBALT(ll) COMPLEXES.

Two examples of radical reactions involving cobalt complexes are described.The first one concerns the reactions of allylcobaloximes with 2-bromo 2-phenylacetonitriles leading to the corresponding monoallyl derivatives.It is shown that both the rate and regioselectivity of the reactions are affected by the nature of the substituents on the phenyl group : electron-withdrawing groups give higher rates and highly regiospecific reactions.The second type of radical reactions wich finds useful synthetic applications is the oxidation of phenols by O2 catalysed by Schiff base cobalt complexes.By choosing carefully the catalyst and the solvent, these oxidations can be highly selective, quinones being the major oxidation products in most cases.

Reactions of Trimethylsilyl Cyanide and N-(Trimethylsilyl)diphenylmethyleneamine with Nitrones and Thermal Decompositions of Their Adducts

Trimethylsilyl cyanide (1) and N-(trimethylsilyl)diphenylmethyleneamine (2) reacted with α-aryl-N-phenylnitrones to afford the corresponding 1:1 adducts 4 and 5 respectively.Thermal decomposition of 4 in refluxing xylene gave azoxybenzene, stereoisomers of 2,3-diarylsuccinonitriles, α-aminonitriles and/or benzanilides, whose yields depended on the nature of substituents on phenyl group of 4.On heating in benzene 5 afforded a mixture of azoxybenzene and meso-N,N'-bis(diphenylmethylene)-1,2-diarylethylenediamines.On the other hand, reactions of 1 and 2 with N-(diphenylmethylene)aniline N-oxide or N-(9-fluorenylidene)aniline N-oxide did not give the corresponding 1:1 adducts, but instead compounds arising from thermal decomposition of initial 1:1 adducts were directly obtained.The reaction of 1 with N-(p-diethylaminophenyl)-α-phenylnitrone leading to the corresponding α-imino nitrile is also described.