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Synthesis of 6,8-substituted-5,7-difluoro-3,4-dihydro-1H-quinoxalin-2-ones via reductive cyclisation of 2,4,6-substituted-3,5-difluoronitrobenzenes

Lookup NU author(s): Dr Ian HardcastleORCiD

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Abstract

The synthesis of substituted 5,7-difluoro-3,4-dihydro-1H-quinoxalin-2-ones is described via reductive cyclisation of 2,4,6-substituted-3,5-difluoronitrobenzenes. Reliable conditions for the reduction of solid-phase bound 2,4,6-substituted-3,5-difluoronitrobenzenes were not found. In contrast, solution-phase reductions proceeded smoothly giving the cyclised quinoxalin-2-one products in good yields. A method optimised for rapid parallel synthesis is described, using zinc in acetic acid as reductant, which has been demonstrated to be general for products bearing a range of substituents. (C) 2002 Elsevier Science Ltd. All rights reserved.

Publication metadata

Author(s): Holland RJ, Hardcastle IR, Jarman M

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2002

Volume: 43

Issue: 36

Pages: 6435-6437

ISSN (print): 0040-4039

ISSN (electronic): 1873-3581

URL: http://dx.doi.org/10.1016/S0040-4039(02)01363-1

DOI: 10.1016/S0040-4039(02)01363-1

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