4293-74-7

Upstream product

• 55110-58-2 3-methyl-1-phenyl-2,5-dihydro-1H-pyrrole 
• 586-96-9 Nitrosobenzene 
• 839705-26-9 gleinadiene 
• 14465-74-8 N-phenyl-N-prop-2-ynylamine 
• 109-92-2 ethyl vinyl ether 
• 589-09-3 N-allyl-N-phenylamine 
• 62-53-3 aniline 
• 15885-06-0 1-[methyl(phenyl)amino]propan-2-one 

Relevant academic research and scientific papers

Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds

A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp2 boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp3 boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. 1H and 11B NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition-elimination sequence.

Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis-aromatization sequence.

A ring closing metathesis-manganese dioxide oxidation sequence for the synthesis of substituted pyrroles

The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were obtained for a variety of substituents and the procedure may also be conducted in one-pot. 2-Bromo N-sulfonyl adducts prepared in this manner were subjected to an intramolecular Heck-type cyclisation, forming cyclic sulfonamides.

Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis-Cyclization Reaction

Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted pyrroles. The value of the methodology is further corroborated by the conversion of pyrroles into 3-methyl-pyrrolines and the derivatization of the 3-methyl-substituent arising from the metathesis reaction.

A novel, efficient synthesis of N-aryl pyrroles via reaction of 1-boronodienes with arylnitroso compounds

A one-pot hetero-Diels-Alder/ring contraction cascade is presented from the reaction of 1-boronodienes and arylnitroso derivatives to derive N-arylpyrroles in moderate to good yields (up to 82%).

Synthesis of pyrrole derivatives from diallylamines by one-pot tandem ring-closing metathesis and metal-catalyzed oxidative dehydrogenation

A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl 3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles in the proposed catalytic system.

The cheletropic ene-reaction and its reversal; additions to 1,2,3,4-tetrachloro-5-methylenecyclohexa-1,3-diene

The cheletropic ene-reaction is presented as an extension of the known pericyclic additions. No example of this process is known but some decarbonylations have been discussed as its reverse. The scope of these reactions is extended by the facile decarbonylation of the alicyclic trienal 11 to give o-xylene. The dramatic lowering of the activation energy when an arene is formed and the finding that in this system phenyl isocyanide can also act as a chelefuge underline the pericyclic character of this reaction. In quest of a cheletropic addition to an ene 1,2,3,4-tetrachloro-5-methylenecyclohexa-1,3-diene was reacted with CO under pressure but to no avail. The reactive ene however readily adds an electron deficient ketone and molecular oxygen.

Reaction of lithium trimethylsilyldiazo-methane with n,n-dialkylamides of α-keto acids and n,n-disubstituted α-amino ketones

Lithium trimethylsilyldiazomethane smoothly reacted with N ,N -dialkylamides of α-keto acids and N ,N-disubstituted α-amino ketones to give 2-oxo-3-pyrrolines and 3-pyrrolines, respectively, in good to moderate yields.