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

✍ Scribed by Deodialsingh Guiadeen; Shankaran Kothandaraman; Lihu Yang; Sander G. Mills; Malcolm MacCoss

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
167 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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