36929-60-9

Upstream product

• 96-54-8 N-Methylpyrrole 
• 3724-43-4 Vilsmeier reagent 
• 68-12-2 N,N-dimethyl-formamide 
• 4497-57-8 2,2,4-trimethyl-3,4-dihydroquinoline-1(2H)-carbaldehyde 
• 2700-30-3 N,N-diisorpopylformamide 
• 607-00-1 diphenylformamide 
• 52008-97-6 N-isopropyl-N-phenylformamide 
• 54262-97-4 2,2,6,6-tetramethylpiperidine-1-carboxaldehyde 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 143817-20-3 [4-(3,3-Diphenyl-propionyl)-piperazin-1-yl]-(1-methyl-1H-pyrrol-3-yl)-acetonitrile 
• 36929-61-0 1-methyl-pyrrole-3-carboxylic acid 
• 1067249-58-4 2-(2,2-dibromovinyl)-N-[(1-methyl-1H-pyrrol-3-yl)methyl]aniline 
• 1124239-65-1 C₂₈H₂₉N₅ 
• 1244386-82-0 2-bromo-N-[(1-methyl-1H-pyrrol-3-yl) methylene]aniline 

Relevant academic research and scientific papers

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

Direct and efficient synthesis of pyrrole-3-carbaldehydes by Vilsmeier-Haack formylation of pyrroles with sterically crowded amides

A simple and convenient synthetic method to prepare N-substituted pyrrole-3-carbaldehydes by Vilsmeier-Haack formylation of pyrroles using sterically crowded formamides was developed. The dependence of the formylation regioselectivity on steric features of substrates and reagents is discussed. Georg Thieme Verlag Stuttgart · New York.

REDUCTIONS OF 3-(N-ARYLAMINOMETHYLENE)SUCCINIMIDES

The reduction Z-N-methylanilinomethylene-N'-phenylsuccinimide is reported and, depending on the conditions, a variety of products may be formed in reasonable yield.For example, the regioselectivity of the NaBH4/EtOH reduction is different from that predicted in the literature, and LAH reduction under mild conditions gives N-phenylpyrrole-3-carboxaldehyde.

Vilsmeier Formylation and Glyoxylation Reactions of Nucleophilic Aromatic Compounds Using Pyrophosphoryl Chloride

Reactions of N,N-dimethylformamide and N-methylformanilide with pyrophosphoryl chloride lead to the formation of reagents that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy-substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the preparation of methyl arylglyoxylates. Key words: pyrophosphoryl chloride, N,N-dimethylformamide, methoxyarene, heterocyle, formylation