64792-80-9

Upstream product

• 98-88-4 benzoyl chloride 
• 22483-09-6 2,2-dimethoxyethylamine 
• 645-36-3 2,2-diethoxy-ethanamine 
• 487-89-8 Indole-3-carboxaldehyde 
• 88333-03-3 Benzyl isocyanide 
• 65-85-0 benzoic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 81912-53-0 4(S)-(methoxycarbonyl)-N-benzoyl-1,3-oxazolidine-2-thione 
• 81925-64-6 methyl 3-benzoyl-2-thioxothiazolidine-4-carboxylate 

Downstream Products

• 6542-76-3 2-(benzoylamino)acetaldehyde 
• 199918-46-2 N-(2,2-dimethoxyethyl)-N-(prop-2-ynyl)benzamide 
• 853688-08-1 C₁₂H₁₅NO₄ 
• 54879-88-8 N-benzyl-2,2-dimethoxyethylamine 
• 99682-51-6 phenyl(2-phenyl-1H-pyrrol-1-yl)methanone 

Relevant academic research and scientific papers

N-Acylethanolamines as novel alcohol dehydrogenase 3 substrates

N-Acylethanolamines (NAEs) are members of the fatty acid amide family. The NAEs have been proposed to serve as metabolic precursors to N-acylglycines (NAGs). The sequential oxidation of the NAEs by an alcohol dehydrogenase and an aldehyde dehydrogenase wo

Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides

Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.

Copper-catalyzed oxidative cleavage of Passerini and Ugi adducts in basic medium yielding α-ketoamides

The aerobic oxidative cleavage of Passerini and Ugi adducts in the presence of base and copper(i) iodide is studied in detail. The oxidative cleavage yields α-ketoamides along with acids and amides from Passerini and Ugi adducts respectively. Mechanistic investigations revealed that the reaction proceeds via a radical pathway involving molecular oxygen. Control experiments with 18O-labeled Passerini adducts confirmed that molecular oxygen is the source of oxygen in α-ketoamides. A variety of Passerini and Ugi adducts were studied to explore the effect of substitution. Overall, the present study provides an insight into the reactivity of Passerini and Ugi adducts in strong basic conditions along with a method to prepare α-ketoamides.

Autotandem catalysis: Synthesis of pyrroles by gold-catalyzed cascade reaction

A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.

Modulating reactivity and diverting selectivity in palladium-catalyzed heteroaromatic direct arylation through the use of a chloride activating/blocking group

(Chemical Equation Presented) Through the introduction of an aryl chloride substituent, the selectivity of palladium-catalyzed direct arylation may be diverted to provide alternative regioisomeric products in high yields. In cases where low reactivity is typically observed, the presence of the carbon-chlorine bond can serve to enhance reactivity and provide superior outcomes. From a strategic perspective, the C-Cl bond is easily introduced and can be employed in a variety of subsequent transformations to provide a wealth of highly functionalized heterocycles with minimal substrate preactivation. The impact of the C-Cl functional group on direct arylation reactivity has also been evaluated mechanistically, and the observed reactivity profiles correlate very well with that predicted by a concerted metalation-deprotonation pathway.

Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides: Application to the synthesis of disubstituted ynamides

β,β-Dihaloenamides can be successfully involved in palladium-catalyzed Suzuki-Miyaura coupling reactions. Whereas the resulting tri substituted (Z)-β-bromoenamides could participate in a second cross-coupling leading to β,β-disubstituted enamides, the (Z)-β-chloroenamides have been converted to disubstituted ynamides by an E2 elimination.

The use of thioesters in solid phase organic synthesis

Mercaptan-resin linkers are used for the synthesis of C-terminal thioesters which are then cleaved with alcohols, amines and organometallic reagents to generate esters, amides, ketones, aldehydes and alcohols as the final products of solid phase synthesis

Nickel-catalyzed heterocycle construction with stereoselective exocyclic alkene introduction

A series of monocyclic and bicyclic heterocycles with exocyclic alkenes were constructed in a stereoselective fashion by an organozinc/Ni(COD)2 - mediated cyclization of alkynyl enones. Both reductive and alkylative cyclization manifolds were accessible depending on the ligand and organozinc structure. Alkylative cyclizations were generally more efficient than reductive cyclizations, particularly with cyclic substrates.