99553-79-4

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 302-72-7 rac-Ala-OH 
• 93709-64-9 (S)-2-(4-methoxybenzamido) propanoic acid 
• 125700-05-2 2-(4-Methoxy-benzoylamino)-propionic acid methyl ester 

Downstream Products

• 143947-53-9 3-(N-p-Anisoylamino)-N-p-methoxyphenyl-3-methyl-4-(4-oxobenzopyran-3-yl)azetidin-2-one 
• 108463-02-1 N-(1-Cyclohexyl-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)-4-methoxy-benzamide 
• 85380-81-0 4-Methoxy-N-(3-methyl-2-oxo-1,4-diphenyl-1,2,3,4-tetrahydro-pyridin-3-yl)-benzamide 
• 85380-82-1 N-[1-(4-Chloro-phenyl)-3-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyridin-3-yl]-4-methoxy-benzamide 
• 85393-36-8 4-Methoxy-N-[1-(4-methoxy-phenyl)-3-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyridin-3-yl]-benzamide 
• 142779-75-7 1,2-diphenyl-5-methyl-4-methylthio-5-p-methoxybenzoylamino-4-piperidino-1,4,5,6-tetrahydropyrimidin-6-one 
• 142779-72-4 1,2-diphenyl-5-methyl-4-methylthio-5-p-methoxybenzoylamino-4-morpholino-1,4,5,6-tetrahydropyrimidin-6-one 
• 142779-64-4 4-dimethylamino-5-methyl-2-methylthio-5-p-methoxybenzoylamino-1-phenyl-1,4,5,6-tetrahydropyrimidin-6-one 
• 142779-59-7 4-dimethylamino-1,2-diphenyl-5-methyl-5-p-methoxybenzoylamino-1,4,5,6-tetrahydropyrimidin-6-one 
• 142779-60-0 4-dimethylamino-5-methyl-5-p-methoxybenzoylamino-2-phenyl-1-p-tolyl-1,4,5,6-tetrahydropyrimidin-6-one 
• 143947-52-8 3-(N-p-Anisoylamino)-3-methyl-4-(4-oxobenzopyran-3-yl)-N-p-tolylazetidin-2-one 
• 143947-56-2 3-(N-p-Anisoylamino)-N-p-bromophenyl-3-methyl-4-(4-oxobenzopyran-3-yl)azetidin-2-one 
• 3424-93-9 4-methoxyphenylacetamide 
• 73894-89-0 acetyl-p-methoxybenzoylimide 

Relevant academic research and scientific papers

Rational Design of 2-Substituted DMAP- N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones

A novel concept that conversion of chiral 2-substituted DMAP into its DMAP-N-oxide could significantly enhance the catalytic activity and still be used as an acyl transfer catalyst is presented. A new type of chiral 2-substituted DMAP-N-oxides, derived from l-prolinamides, has been rationally designed, facilely synthesized, and applied in the dynamic kinetic resolution of azlactones. Using simple MeOH as the nucleophile, various l-amino acid derivatives were produced in high yields (up to 98% yield) and enantioselectivities (up to 96% ee). Furthermore, α-deuterium labeled l-phenylalanine derivative was also obtained. Experiments and DFT calculations revealed that in 2-substituted DMAP-N-oxide, the oxygen atom acted as the nucleophilic site and the N-H bond functioned as the H-bond donor. High enantioselectivity of the reaction was governed by steric factors, and the addition of benzoic acid reduced the activation energy by participating in the construction of a H-bond bridge. The theoretical chemical study indicated that only when attack directions of the chiral catalyst were fully considered could the correct calculation results be obtained. This work paves the way for the utilization of the C2 position of the pyridine ring and the development of chiral 2-substituted DMAP-N-oxides as efficient acyl transfer catalysts.

Catalytic Aerobic Cross-Dehydrogenative Coupling of Azlactones en Route to α,α-Disubstituted α-Amino Acids

We developed a catalytic aerobic method to synthesize α,α-disubstituted α-amino acids through cross-dehydrogenative coupling of azlactones. Combining an iron catalyst with a bisoxazolidine ligand resulted in high catalytic performance, and cross-coupling with an indole proceeded smoothly under aerobic conditions. A wide variety of α-aryl and aliphatic amino acid derived azlactones were applied to the present catalysis. In addition, a quaternary carbon could be constructed using oxindole and benzofuranone under aerobic conditions.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Synthesis of di- and tri-substituted imidazole-4-carboxylates via PBu3-mediated [3+2] cycloaddition

Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole- 4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated Δ2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Bispalladacycle-catalyzed Michael addition of in situ formed azlactones to enones

The development and further evolution of the first catalytic asymmetric conjugate additions of azlactones as activated amino acid derivatives to enones is described. Whereas the first-generation approach started from isolated azlactones, in the second-generation approach the azlactones could be generated in situ starting from racemic N-benzoylated amino acids. The third evolution stage could make use of racemic unprotected α-amino acids to directly form highly enantioenriched and diastereomerically pure masked quaternary amino acid products bearing an additional tertiary stereocenter. The step-economic transformations were accomplished by cooperative activation by using a robust planar chiral bis-Pd catalyst, a Br?nsted acid (HOAc or BzOH; Ac=acetyl, Bz=benzoyl), and a Br?nsted base (NaOAc). In particular the second- and third-generation approaches provide a rapid and divergent access to biologically interesting unnatural quaternary amino acid derivatives from inexpensive bulk chemicals. In that way highly enantioenriched acyclic α-amino acids, α-alkyl proline, and α-alkyl pyroglutamic acid derivatives could be prepared in diastereomerically pure form. In addition, a unique way is presented to prepare diastereomerically pure bicyclic dipeptides in just two steps from unprotected tertiary α-amino acids. Flourishing step economy: The evolution of the catalytic asymmetric addition of azlactones to enones is described. The first-generation approach started from isolated azlactones. In the second-generation approach azlactones could be generated in situ from racemic N-benzoylated amino acids. The third evolution stage could directly use racemic unprotected α-amino acids to form a large number of highly enantioenriched quaternary amino acids derivatives (see figure). Copyright

1-Azadienes in Heterocyclic Synthesis. Reaction of 1-N-Alkyl-1-azapenta-1,3-dienes with Mesoionic Oxazolones

1-N-Alkyl-1-azapenta-1,3-dienes 2 smoothly reacted with various mesoionic oxazolones 1 to afford 3,4-dihydro-2-pyridones 3 in excellent yields and there is no evidence for the formation of any products arising from the cycloaddition on the carbon-carbon double bond or on the azomethine function.

Cycloaddition Reactions of Mesoionic Oxazolones. Reactions of Δ2-Oxazolin-5-one with Cinnamaldehyde Anils

Cinnamaldehyde anils have been reacted with several mesoionic oxazolones.The products thus obtained are α-pyridones and structures of these compounds have been fully established.