ABSTRACT
An unexpected C-C bond cleavage has been observed on pentafluorobenzoylamidoximes under mild basic conditions. This observation has been exploited to develop a new synthesis of 1,2,4-oxadiazol-5-ones from amidoximes using pentafluorobenzoyl chloride or trifluoroacetic anhydride (TFAA) as a double acylating agent. The pentafluorophenyl anion and the trifluoromethyl anion acted as leaving groups in this transformation.
ABSTRACT
A useful method to construct highly substituted tetrahydroquinolines has been developed through an iron(III) chloride-mediated domino Mannich and intramolecular Friedel-Crafts alkylation followed by intermolecular Friedel-Crafts alkylation reactions of aliphatic aldehydes with aromatic amines.
Subject(s)
Aldehydes/chemistry , Amines/chemistry , Chlorides/chemistry , Ferric Compounds/chemistry , Quinolines/chemical synthesis , Crystallography, X-Ray , Models, Molecular , Molecular Structure , Quinolines/chemistry , StereoisomerismABSTRACT
Cyclisative carbo-iodination of N-alkyl-N-arylacrylamide derivatives (3) in the presence of PhI(OAc)(2)/I(2) afforded functionalized 3-(iodomethyl)-3-substituted-indolin-2-ones (4) in good to excellent yields. With a suitably functionalized linear amide, spirooxindole 8 was prepared in a one-pot fashion via a sequence of iodo-arylation followed by an in situ base-promoted intramolecular S(N)2 reaction.
Subject(s)
Alkenes/chemistry , Indoles/chemical synthesis , Spiro Compounds/chemical synthesis , Cyclization , Electrons , Molecular Structure , OxindolesABSTRACT
A palladium-catalyzed oxidative carbo-heterofunctionalization of aniline derivatives involving concomitant direct C-H functionalization and C-X bond formation was developed. By simply changing the reaction conditions (solvent and catalyst), either 3,3'-disubstituted oxindole or spirooxindole was accessible from the same starting material.
Subject(s)
Alkenes/chemistry , Indoles/chemical synthesis , Palladium/chemistry , Spiro Compounds/chemical synthesis , Catalysis , Cyclization , Oxidation-Reduction , OxindolesABSTRACT
At present, more than 100 strains of Lentinula edodes are cultivated on a commercial scale in China. A simple, reliable, and effective method to distinguish some commercial strains of the superior type from other commercial strains is very important for the Lentinula industry. In this study, 23 commercial strains of L. edodes cultivated widely in China at present were collected and analyzed with randomly amplified polymorphic DNA (RAPD) technique. Three informative dominant sequence characterized amplified region (SCAR) markers were developed by designing three pairs of specific SCAR primers from three sequenced differential RAPD bands, respectively. Based on the three SCAR markers, three different multiplex polymerase chain reaction (PCR) phenotypes were detected among the 23 studied commercial strains and in which a multilocus phenotype characterizing a commercial strain Cr02 of the superior type could potentially be used to distinguish this strain from the other 22 studied commercial strains. To our knowledge, this study is the first to describe the development of a multiplex PCR technique based on SCAR markers for detecting the molecular phenotypes among commercial strains of L. edodes in China.
Subject(s)
Genetic Markers , Polymerase Chain Reaction/methods , Shiitake Mushrooms/classification , Shiitake Mushrooms/genetics , China , DNA Fingerprinting , DNA Primers/genetics , DNA, Fungal/genetics , Genotype , Random Amplified Polymorphic DNA TechniqueABSTRACT
A facile and efficient synthesis of 1,3-diaryl-5-spirohexahydropyrimidines via a one-pot condensation of anilines, formaldehyde, and cyclohexanones is reported. In this one-pot, three-component reaction, six molecules of reactants are involved and six new covalent bonds are generated. Bicyclic products are obtained from the starting materials in one pot using readily available starting materials and catalysts.
