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Synlett 2012; 23(17): 2526-2530
DOI: 10.1055/s-0032-1317181
DOI: 10.1055/s-0032-1317181
letter
Chemo- and Regioselective 4CR Synthesis of Oxathiaaza[3.3.3]propellanes via Sequential C–S, C–N and C–O Bond Formation in a Single Pot
Weitere Informationen
Publikationsverlauf
Received: 23. Juli 2012
Accepted after revision: 14. August 2012
Publikationsdatum:
21. September 2012 (online)


Abstract
Oxathiaaza[3.3.3]propellane derivatives were prepared by reaction of in situ generated asymmetric thioureas with intermediate Knoevenagel adducts resulting from ninhydrin and malononitrile. This four-component sequential transformation performed in one reaction flask represents a general route to this unexplored valuable class of sulfur–nitrogen heterocycles. The chemoselectivity and regiochemistry of the products were established by IR, NMR and single crystal X-ray analysis.
Key words
chemoselectivity - regioselectivity - oxathiaaza[3.3.3]-propellanes - four-component reaction (4CR)Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information