Starting from acid chlorides, alkynes, tryptamines, and acryloyl chloride, 21 densely substituted tetrahydro-β-carbolines were prepared in a four-component, one-pot reaction. In this study, the aza-Michael addition step to generate intermediate enaminones was optimized presence of ytterbium triflate. Moreover, apart all reactants could be deployed almost equimolar ratios, which increases atom e...

We describe here an atom efficient procedure to prepare selenol esters in good to excellent yields by reacting [(PhSe)₂Zn] or [(PhSe)₂Zn]TMEDA with acyl chlorides under "on water" conditions. The method is applicable to a series of aromatic and aliphatic acyl chlorides and tolerates the presence of other functionalities in the starting material.

A novel Pd-catalyzed intermolecular dehydrogenative annulation of aryl iodides and aryl carbamic chlorides for the efficient synthesis of phenanthridinone derivatives was developed. Simple aryl iodides and carbamic chlorides readily made from various anilines, a broad substrate scope with hetero/polycycles, as well as high-value products, make this direct dehydrogenative annulation approach ver...

Simple, efficient procedures for the monoarylation of acetate esters and aryl methyl ketones using aryl chlorides are presented. Previously, no general method was available to ensure the highly selective monoarylation of these classes of substrates using aryl chlorides. Using palladium precatalysts recently reported by our group, these reactions are easily accomplished under mild conditions tha...

WITH THE growing interest in the metabolism of cholesterol esters, procedures have been developed which frequently make desirable the use of chemically pure compounds. Some of the radioactive cholesterol esters are either commercially unavailable or expensive when made to order. The high cost of the starting materials (cholesterol-4-CI4, pure fatty acids) makes it desirable to have a good yield...

A new series of 6-substituted-4-methyl-3-(4-arylpiperazin-1-yl)cinnolines 8-10 were synthesized as potential antifungal agents via intramolecular cyclization of the respective 1-(2-arylhydrazono)-1-(4-arylpiperazin-1-yl)propan-2-ones 5-7, mediated by polyphosphoric acid (PPA). The amidrazones themselves were synthesized via direct interaction of the appropriate hydrazonoyl chlorides 4a-d with t...

Palladium complexes of two new types of unsymmetrical pyridyl-supported pyrazolyl-N-heterocyclic carbene ligands were synthesized and structurally characterized. A strategy to release the steric strain of the ligand was realized by the introduction of methylene linkers to the ligand molecule. All the palladium complexes exhibited good to excellent catalytic activity in Suzuki-Miyaura reactions ...

From the time immemorial, sodium borohydride has been used for the reagent of choice for reducing various carbonyl compounds and acid chlorides in protic solvents. Over the past decades the utility of sodium borohydride has been greatly expanded and various modifications have been developed. Reductive dechlorination of aromatic halo nitro compounds have a great significance in the field of orga...

Olefin cross-metathesis has been demonstrated to be a modular pathway for synthesis of a series of functionalized cellulose esters. As a proof of concept, cellulose acetate was acylated with two terminally olefinic acid chlorides, pent-4-enoyl chloride and undec-10-enoyl chloride, providing olefin-terminated cellulose esters with different side-chain lengths. These ω-unsaturated cellulose ester...

Two new photoreactive arylsulfenyl chlorides, 2-nitro-4-azidophenylsulfenyl chloride (2,4-NAPS-Cl) and 2-nitro-5-azidophenylsulfenyl chloride (2,5-NAPS-Cl), have been synthesized and used for the selective modification of corticotropin (ACTH). Both reagents reacted rapidly with N-acetyltryptophanamide and ACTH under acidic conditions. The NAPS derivatives of ACTH were purified by partition chro...