Joseph M. Muchowski

Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines

Abstract A series of anilines and heteroarylamines were synthesized in moderate to excellent yields by palladium catalyzed cross coupling reaction of aryl or heteroaryl halides with allyl- or N,N-diallylamine followed by deallylation.

A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole

Abstract The AIBN-induced radical reaction of 1-(2-iodoethyl)indoles and pyrroles with Bu 3 SnH under 80 atm of CO was examined. Carbon monoxide was efficiently trapped by an alkyl radical to form an acyl radical which underwent intramolecular addition to the aromatic system to produce bicyclic aromatic ketones after in situ oxidation.

A tandem radical addition/cyclization process of 1-(2-iodoethyl)indoles and methyl acrylate

Abstract Benzindolizidine systems are generated in moderate yields by a hexabutylditin mediated consecutive radical addition, cyclization, oxidation process from 1-(2-iodoethyl)indoles and methyl acrylate.

Intramolecular radical acylation of 2-methylsulfonylpyrroles

Abstract Primary alkyl radicals generated (AIBN/Bu 3 SnH) from 1-(2- or 3-haloalkyl)-2-methylsulfonylpyrroles are intercepted by CO (80 atm), and the acyl radicals so produced undergo intramolecular oxidative cyclization at the α-position, giving bicyclic ketones with retention or loss of the sulfonyl moiety.

Synthesis of tricyclic-2-aminoindoles by intramolecular 1,3-dipolar cycloaddition of 1-ω-azidoalkylindoles

Abstract Thermolysis of the 1-ω-azidoalkylindoles 4 , bearing an electron attracting substituent at C-3 (CHO, COMe, COOMe, CN) provides imidazo[1,2- a ]indoles ( 5 , n =1), pyrimidino[1,2- a ]indoles ( 5 , n =2), and 1,3-diazepino[1,2- a ]indoles ( 5 , n =3).

Novel synthesis of α-diazoketones from acyloxyphosphonium salts and diazomethane

Abstract A novel, simple and mild method to prepare α-diazoketones from carboxylic acids is presented. The procedure involves the reaction of carboxylic acids with triphenylphosphine/NBS and subsequent treatment with diazomethane. 13 C and 31 P NMR experiments demonstrate that the process occurs through an acyloxyphosphonium salt as a key intermediate.