Download PDF
Synfacts 2010(8): 0879-0879  
DOI: 10.1055/s-0030-1257845
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

One-Step Synthesis 3-Nitroisoxazoles

Contributor(s): Victor Snieckus, Toni Rantanen
Y. A. Volkova, E. B. Averina*, Y. K. Grishin, P. Bruheim, T. S. Kuznetsova, N. S. Zefirov
Lomonosov Moscow State University, Russia; Norwegian University of Science and Technology, Trondheim, Norway
Further Information

Publication History

Publication Date:
22 July 2010 (online)

    Permissions and Reprints

Significance

Reported is a general method for the synthesis of 3-nitroisoxazoles by reacting activated (Et3N) tetranitromethane with various α,β-unsaturated compounds containing an electron-withdrawing group. Thus, α,β-unsaturated ketones, aldehydes, carboxylic acid esters, amides, and nitroalkenes were all successfully reacted to form the corresponding substituted 3-nitroisoxazoles. The substrate scope was well studied and the yields range from poor to good. The least ­succesful reaction was that with acrylic amides, which in six out of seven examples led to mixtures of isoxazole and Michael addition products (A and B, respectively).