126381-47-3

Upstream product

• 70-11-1 α-bromoacetophenone 
• 2295-35-4 pyrrolidin-2-thione 
• 3282-32-4 2-diazo-acetophenone 
• 175025-74-8 3-{2-[(E)-2-oxo-2-phenylethylidene]-1-pyrrolidinyl}propanenitrile 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 98-88-4 benzoyl chloride 
• 94532-49-7 [2-(Diphenyl-phosphinoyl)-pyrrolidin-1-yl]-phenyl-methanone 
• 108078-42-8 1-benzoyl-2-methylenetetrahydropyrrole 
• 130721-70-9 3-Oxo-3-phenyl-2-pyrrolidin-(2E)-ylidene-propionic acid methyl ester 

Relevant academic research and scientific papers

Base-Mediated Cyclization of 3-[2-(2-Oxo-2-phenylethyl)-1-pyrrolidinyl]propanenitrile to 7-Phenyl-1,2,3,7,8,8a-hexahydroindolizine-6-carbonitrile: What Lies Between?

Three intermediates along the reaction path by which 3-[2-(2-oxo-2-phenylethyl)-1-pyrrolidinyl]propanenitrile is converted into the rel-(7R,8aR)- and (7R,8aS)-diastereoisomers of 7-phenyl-1,2,3,7,8,8a-hexahydroindolizine-6-carbonitrile upon treatment with

Enaminones via ruthenium-catalyzed coupling of thioamides and α-diazocarbonyl compounds

Enaminones can be prepared via the Rh2(OAc)4- catalyzed coupling of α-diazocarbonyl compounds with thioamides. However, rhodium is the most expensive and least abundant among the dominant precious metals used for catalysis. Furthermore, a very limited substrate scope is known for the intermolecular rhodium catalyzed coupling reaction. Therefore, there is a need to find a more economical catalyst substitute with a broad substrate scope. In this paper, we describe the use of Ru(II) catalysts for the synthesis of enaminones. The reaction can be performed efficiently with the Grubbs first-generation catalyst or [(Ph)3P]3RuCl2 in a sealed tube. Both catalysts are much less expensive than Rh 2(OAc)4. Secondary and tertiary thioamides, when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, and α-diazomonoketones give enaminones. Primary thioamides give thiazole derivatives when reacted with α-diazomonoketones. However, with other diazo compounds, primary thioamides also give enaminones. All enaminones are obtained in good yields and with good diastereoselectivity. Accordingly, the method described in this paper is an efficient and economical alternative to the Rh2(OAc)4-catalyzed coupling process.

One-pot eschenmoser episulfide contractions in DMSO: Applications to the synthesis of fuligocandins A and B and a number of vinylogous amides

Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DMSO proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2- ylidenepropan-2-one. 2011 American Chemical Society.

A convenient protocol for the alkylidenation of lactams

A convenient two-step preparation of alkylidenepyrrolidines is reported. Georg Thieme Verlag Stuttgart.

Dramatically different photochemical behaviour of 1-aroyl-2-methylene piperidine and pyrrolidine derivatives. An expeditious synthesis of ruspolinone

Upon irradiation in neutral solvent, the diversely substituted 1-aroyl-2-methylenepiperidines 6a-f give rise to photocyclized products 4a-f while their pyrrolidine congeners 7a,c,d afford enaminoketones 18a,c,d products of photo-Fries rearrangement.

Chemoselective reactions of vinylogous amides, and the synthesis of two Peripentadenia alkaloids

Some chemoselective transformations of the vinylogous amide (E)-2-benzoylmethylene-1-(2-cyanoethyl)pyrrolidine (3a) and compounds derived from it have been investigated. Methodology developed during the course of these model studies has been applied to th

DECARBOXYLATION OF CYCLIC β-ENAMINOKETOESTERS WITH BORIC ACID

Cyclic β-enaminoketoesters prepared by condensation between lactim ethers and β-ketoesters are decarboxylated without deacylation by thermolysis in presence of boric acid to lead stereospecifically to cyclic β-enaminones.