ABSTRACT
A family of biaryl phosphacyclic ligands derived from phobane and phosphatrioxa-adamantane frameworks is described. The rigid biaryl phosphacycles are efficient for Suzuki-Miyaura cross-coupling of aryl bromides and chlorides. In particular, coupling reactions of the challenging sterically hindered and heterocyclic substrates were viable at room temperature.
ABSTRACT
Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.
Subject(s)
Amides/chemistry , Chlorides/chemistry , Esters/chemistry , Ferric Compounds/chemistry , Solvents/chemistry , Antitubercular Agents/chemistry , Antitubercular Agents/pharmacology , Catalysis , Lactams/chemical synthesis , Lactams/chemistry , Pyrimidines/chemistry , Pyrimidines/pharmacologyABSTRACT
Correction for 'A convenient domino Ferrier rearrangement-intramolecular cyclization for the synthesis of novel benzopyran-fused pyranoquinolines' by Paseka T. Moshapo et al., Org. Biomol. Chem., 2016, DOI: 10.1039/c5ob02536b.
ABSTRACT
The Ferrier rearrangement and the Povarov reaction have proven indispensable tools in carbohydrate chemistry and the synthesis of N-heterocycles, respectively. We hereby report a one-pot cyclization sequence involving the Ferrier and Povarov-like reactions in the synthesis of novel pentacyclic N-heterocycles: benzopyran-fused pyranoquinolines. The reaction entails three component condensation of a glycal with a variety of anilines and 2-hydroxybenzaldehydes under Lewis acid catalysis to yield the title compounds in 4-24 hours of reaction time, in moderate to high yields and excellent diastereoselectivity. Of the Lewis acid catalysts deployed [Sc(OTf)3, Al(OTf)3, Cu(OTf)2, CuOTf, I2, InCl3, and La(OTf)3] in various solvents (acetonitrile, THF, dichloromethane, 1,2-dichloroethane and diethyl ether) at room and elevated temperatures, Sc(OTf)3 (10 mol%) in acetonitrile at 70 °C gave the best results, with excellent diastereoselectivity. CAN-mediated oxidative ring opening of the pentacyclic N-heterocycle gave the corresponding enantiometrically pure chromenoquinoline bearing a pendant sugar moiety.
ABSTRACT
A novel class of fused thiochroman derivatives has been prepared by an efficient and versatile synthetic procedure involving nucleophilic displacement of the side-chain iodo substituent in 2-deoxy-2-C-iodomethyl glucosides by thiophenolate ions, and subsequent intramolecular C-glycoside formation. A range of aromatic substituents is tolerated, and the subsequent facile selective oxidation of the sulfur to the sulfoxide or sulfone level expands the range and molecular diversity of the series of compounds. A selection of the sulfoxide and sulfone derivatives bearing lipophilic substituents on the aromatic portion were found to have antimalarial activities in the low micromolar range.
Subject(s)
Antimalarials/chemical synthesis , Antimalarials/pharmacology , Carbohydrates/chemistry , Chromans/chemical synthesis , Chromans/pharmacology , Malaria, Falciparum/drug therapy , Cell Proliferation/drug effects , Cells, Cultured , Glycosides , Humans , Molecular Structure , Monosaccharides/chemistry , Plasmodium falciparum/drug effects , Structure-Activity Relationship , Sulfones/chemistryABSTRACT
The pyranosyl ring in the title compound, C(31)H(34)Cl(2)O(7), adopts a twist-boat conformation. The 4-meth-oxy-benzyl groups are located in equatorial positions with the meth-oxy groups nearly coplanar with their respective rings [dihedral angles of 0.2â (3) and 9.4â (2)°]. The aromatic rings adopt orientations enabling them to participate in C-Hâ¯π inter-actions with neighboring meth-oxy groups. The crystal structure is additionally stabilized by weak C-Hâ¯O inter-actions.
ABSTRACT
Authors in this randomised prospective study, which occurred in years 2007 to 2008 on the St. Anne's First Surgical Clinic in 56 breast cancer female patients, compare the results of minimally invasive axillary dissection to those of the classical axillary dissection and point to the advantages and setbacks of this new method both for the patient and surgeon.
Subject(s)
Axilla/surgery , Breast Neoplasms/surgery , Endoscopy , Lymph Node Excision/methods , Adult , Aged , Aged, 80 and over , Female , Humans , Lymphatic Metastasis , Middle Aged , Minimally Invasive Surgical ProceduresABSTRACT
Mirizzi syndrome is a rare complication of the long-term gallbladder stone disease. It's caused by a gallbladder stone impression to the common bile duct wall. The clinical appearance is an obstructive jaundice, pain in right subchondrium and dyspepsia. Higher pressure in the extrahepatal bile ducts leads to biliobiliary or enterobiliary fistula formation. In the described case a cholecystoduodenal fistula was found. Preoperative diagnosis of MS is a medical challenge, and majority of the diagnosis is set introperatively. Surgery is the treatment of first choice. Ignoring the possibility of MS can seriously damage patient's health by injuring bile ducts during the surgery.