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An expeditious synthesis of 3-(difluoromethoxy)- and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines

Guiadeen, Deodialsingh ; Kothandaraman, Shankaran ; Yang, Lihu ; Mills, Sander G. ; Maccoss, Malcolm

Tetrahedron Letters, 2008, Vol.49(44), pp.6368-6370 [Peer Reviewed Journal]

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  • Title:
    An expeditious synthesis of 3-(difluoromethoxy)- and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines
  • Author: Guiadeen, Deodialsingh ; Kothandaraman, Shankaran ; Yang, Lihu ; Mills, Sander G. ; Maccoss, Malcolm
  • Description: A concise synthesis of tetrahydro-naphthyridines bearing 3-difluoro ( 2) and 3-trifluoromethoxy ( 3) substituents is detailed. An expeditious and concise synthesis of 3-(difluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridine and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines is described. Starting from N-benzyl piperidone, the key intermediates leading to these two biologically desirable synthones were rapidly assembled by inverse electron demand Diels–Alder (IEDA) reaction utilizing microwave irradiation. The scope of the microwave methodology developed herein was extended to other ketones.
  • Is Part Of: Tetrahedron Letters, 2008, Vol.49(44), pp.6368-6370
  • Identifier: ISSN: 0040-4039 ; DOI: 10.1016/j.tetlet.2008.08.083
  • Subjects: Difluoromethoxy ; Trifluoromethoxy ; Microwave
  • Language: English

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