58569-87-2

Upstream product

• 75-44-5 phosgene 
• 127-19-5 N,N-dimethyl acetamide 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 67-66-3 chloroform 

Downstream Products

• 58114-25-3 N,N-dimethylaminoethane hydrochloride 
• 932-16-1 N-methyl-2-acetylpyrrole 
• 932-62-7 3-acetyl-1-methyl-1H-pyrrole 
• 1072-83-9 2-Acetylpyrrole 
• 1193-79-9 2-acetyl-5-methylfuran 
• 123-86-4 acetic acid butyl ester 
• 2623-23-6 L-menthyl acetate 
• 5525-85-9 N-Cyclohexylbrenztraubensaeure-amid 

Relevant academic research and scientific papers

1H-1,2,4-diazaphospholes: Synthesis, structural characterization, and DFT calculation

A few 1H-1,2,4-diazaphospholes H[3,5-R2dp] (R = methyl (5a), p-tolyl (5b), 1-naphthyl (5c), 2-furanyl (5d), 2-thienyl (5e), and isopropyl (5f)) were prepared and structurally characterized by a substantial experimental modification of the synth

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.

Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation

A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.

A One-Pot Synthesis of Highly Functionalized Purines

Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

Polycyclic N-heterocyclic compounds. Part 86: Synthesis and evaluation of antiplatelet aggregation activity of 2,4-disubstituted 9-chloro-5,6-dihydropyrimido[5,4-d]benzazepine and related compounds

Libraries of tricyclic 2-substituted 4-alkylamino-9-chloro-5,6-dihydropyrimido[5,4-d]benzazepines and tetracyclic 12-substituted 8-chloro-1,2,5,6-tetrahydro-4H-imidazo[1',2':1,6]pyrimido[5,4-d]benzazepines were synthesized as part of our research to develop new effective antiplatelet drugs. Several alkyl and aryl groups were used as substituents at the 2-position. Evaluation of the effects of the newly synthesized compounds on collagen-induced platelet aggregation revealed several promising antiplatelet candidates with potencies superior to aspirin.

Syntheses of 4-substituted 2-(trichloromethyl)quinazolines under mild conditions by benzyne [4+2] cycloaddition

An experimentally simple and convenient synthesis of 4-susbstituted 2-(trichloromethyl)quinazolines by cycloaddition of benzyne with 2-(trichloromethyl)-1,3-diazabutadienes was developed. The 2-(trichloromethyl)-1,3-diazabutadienes (R1 = H and Me) were prepared from trichloroacetamidine and the appropriate N,N-dimethylamide dimethyl acetal or from trichloroacetamidine and a Vilsmeier-Haack reagent containing an aryl group.

Polycyclic N-heterocyclic compounds. Part 75: Synthesis of 2,4-disubstituted 5,6-dihydro[1]benzoxepino[5,4-d]pyrimidines and 12-substituted 1,2,4,5-tetrahydro[1]benzoxepino[4,5-e]imidazo[1,2-c]pyrimidines as potential antiplatelet aggregators

Libraries of tricyclic 2-substituted 4-alkylamino-5,6-dihydro[1] benzoxepino[5,4-d]pyrimidines and tetracyclic 12-substituted 1,2,4,5-tetrahydro[1]benzoxepino[4,5-e]imidazo[1,2-c]pyrimidines were synthesized as part of our research to develop new effectiv

Improved Synthesis of Asymmetrical Substituted 1 H-1,2,4-Diazaphospholes

The reaction of tris(trimethylsilyl)phosphine and a mixture of two different N,N-dimethylalkylamides (1a,b), followed by the treatment with dry hydrazine in situ, resulted in seven asymmetrical 3,5-disubstituted 1H-1,2,4-diazaphospholes (3a-g). Compounds

Investigations in 2,3′-biquinoline series 24. Synthesis of 3-hetarylquinolines and their 1,4-dihydro derivatives under conditions of the Vilsmeier reaction

Methods have been developed for the synthesis of 2,3′-biquinolines, their 1′,4′-dihydro derivatives, 3-pyrid-2-ylquinolines, and 3-pyrazin-2-ylquinoline based on the interaction of hetarylethylenes and vinyl butyl ether with imidoyl chlorides and Vilsmeie

Asymmetric Synthesis of β-Lactams

The reaction of α-chloroiminium chlorides with imines in which one of the reagent contains a chiral substituent leads diastereoselectively to substituted β-lactams.