Synthesis of naphthyridin-2(1H)-one derivatives via ring expansion of 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives†
Abstract
The reaction of 3-substituted 1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives with sodium azide or azidotrimethylsilane under microwave irradiation provided 3- and 4-amino-naphthyridin-2(1H)-one derivatives through cycloaddition–ring expansion. The insertion of the azide into the α,β unsaturated carbonyl of 3-substituted pyrrolo[2,3-b]pyridin-2(3H)-one derivatives proceeded via an unusual rearrangement. This methodology provided 39 ring expansion examples in moderate to good yields.
![Graphical abstract: Synthesis of naphthyridin-2(1H)-one derivatives via ring expansion of 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C8CC01518J&imageInfo.ImageIdentifier.Year=2018)
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