Current Organic Chemistry

Author(s): Matyas Milen, Peter Abranyi-Balogh, Zoltan Mucsi, Andras Dancso, David Frigyes, Laszlo Pongo and Gyorgy Keglevich

DOI: 10.2174/13852728113179990035

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Synthesis of New β-Carboline Derivatives Fused with β-Lactam Rings: An Experimental and Theoretical Study

Page: [1894 - 1902] Pages: 9

  • * (Excluding Mailing and Handling)

Abstract

The Staudinger reaction of various β-carboline derivatives with aryloxyacetyl chlorides led to novel fused tetracyclic compounds containing two biologically considerable cores, such as the β-carboline and the β-lactam units. The reaction is stereoselective, giving exclusively the cis cycloadducts as racemates. The mechanism and the 100% stereoselectivity of this cycloaddition was studied by high level quantum chemical calculations.

Keywords: Staudinger reaction, β-Carbolines, β-Lactams, Cycloaddition, Mechanism.