83620-45-5

Upstream product

• 288-13-1 NH-pyrazole 
• 102-92-1 cinnamoyl chloride 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 392668-05-2 (+)-(R)-methyl 3-phenyl-3-phenylsulfanylpropanoate 
• 29476-22-0 (R)-2-phenyl-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one 

Relevant academic research and scientific papers

Tuning the Basicity of a Metal-Templated Br?nsted Base to Facilitate the Enantioselective Sulfa-Michael Addition of Aliphatic Thiols to α,β-Unsaturated N-Acylpyrazoles

The enantioselective addition of aliphatic thiols to α,β-unsaturated N-acylpyrazoles catalyzed by a bis-cyclometalated iridium(III) complex with fine-tuned Br?nsted basicity was investigated. Good to excellent yields (71-99 %) and enantioselectivities (86-98 % ee) were achieved at catalyst loadings of 0.2-2.5 mol-%. In this metal-templated catalyst design, the metal serves as a structural center and the catalysis is executed by the organic ligand sphere through a combination of proton transfer, hydrogen-bond formation, and electrostatic interactions.

Nitroxide-Catalyzed Oxidative Amidation of Aldehydes to Yield N-Acyl Azoles Using Sodium Persulfate

A methodology for the oxidative amidation of aldehydes to yield N-acyl azoles is reported. The approach employs sodium persulfate and a catalytic amount of a nitroxide and is applicable to a range of structurally diverse substrates.

Cu(i)-Catalyzed asymmetric: Exo -selective synthesis of substituted pyrrolidines via a 1,3-dipolar cycloaddition reaction

An (R)-DM-BINAP/Cu(CH3CN)4BF4 complex catalyzed exo-selective asymmetric 1,3-dipolar cycloaddition (1,3-DCA) reaction of imino esters with α,β-unsaturated pyrazoleamides has been developed. A series of highly functionalized pyrrolidines with multiple stereogenic centers were obtained with good yields and diastereoselectivities and excellent enantioselectivities (up to 99% ee).

(R)-DM-SEGPHOS-Ag(I)-Catalyzed Enantioselective Synthesis of Pyrrolidines and Pyrrolizidines via (1,3)- and Double (1,3)-Dipolar Cycloaddition Reactions

An efficient diastereo- and enantioselective route to access a wide range of highly substituted pyrrolidine and pyrrolizidine derivatives has been described via (1,3)- and double (1,3)-dipolar cycloaddition reactions catalyzed by the (R)-DM-SEGPHOS-Ag(I) complex. The reactions proceed smoothly at ambient temperature, affording a variety of pyrrolidines and pyrrolizidines in high yields (up to 93%) with up to 99:1 dr and excellent enantioselectivities (up to 98% ee) without any additives. The newly synthesized pyrrolidine and pyrrolizidine derivatives contain four and seven contiguous stereogenic centers, respectively. Moreover, the synthetic utility of enantioenriched products has been demonstrated by transforming them into various synthetically useful advanced intermediates.

Catalytic Enantioselective Synthesis of Protecting-Group-Free 1,5-Benzothiazepines

A one-pot enantioselective route to N-unprotected 2,3-dihydro-1,5-benzothiazepinones, by an organocatalyzed sulfa-Michael reaction of readily available α,β-unsaturated N-acyl pyrazoles with 2-aminothiophenols followed by silica-gel-catalyzed lactamization

Accessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation

An operationally simple, robust, metal-free approach to the synthesis of N-acyl azoles from both alcohols and aldehydes is described. Oxidative amidation is facilitated by a commercially available organic oxidant (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and proceeds under very mild conditions for an array of structurally diverse substrates. Tandem reactions of these activated amides, such as transamidation and esterification, enable further elaboration. Also, the spent oxidant can be recovered and used to regenerate the oxoammonium salt.

Methyleneketenes and Methylenecarbenes. XVII Generation of Methyleneketene Intermediates by Pyrolysis of N-Alkenoylpyrazoles and Synthesis of Simple Phenols

Flash vacuum pyrolysis of 1-acyl-3,5-dimethylpyrazoles forms ketenes, but the conditions may lead to decarbonylation of the ketene.The 1-cinnamoyl derivative (4) forms phenylacetylene at 750 deg/0.02 mm, via benzylideneketene and benzylidenecarbene.Simple phenols (2-naphthol, phenol, 4-methylphenol, 2,4-dimethylphenol, and 3,5-dimethylphenol) are obtained in high yield on pyrolysis of the appropriate dienoylpyrazoles (10), (13), (16), (18) and (21); the reaction proceeds by way of cyclization of dienylketenes.