One-Pot Cascade Transformation of Glucal into Structurally Diverse Drug-Like Scaffolds.

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ID: 56910
2019
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Abstract
A diversity-oriented synthesis strategy to produce three types of structurally drug-like N-heterocyclic-fused rings has been developed from abundant biomass-derived d-glucal, aniline and water in a stereoselective manner. The overall transformation which entails a cascade of Ferrier reaction and 4π conrotatory imino-Nazarov cyclization was performed in one-pot allowing convenient preparation of scaffolds of high molecular complexity from relatively simple starting materials. While indoline-fused products were readily accessible using ortho-unsubstituted secondary anilines as substrates, reactions with ortho-hydroxyl-anilines furnished fused 1,4-benzoxazines instead. In both cases, InBr acted as the Lewis acid catalyst. By altering InBr to Ln(OTf) , the indoline-fused products could be further converted into tetrahydroquinoline-fused cyclopentenones via ensuing retro-ene rearrangement.
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yao2019onepotchemistry Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Yao, Hui;Willam, Ronny;Wang, Siming;He, Jingxi;Guo, Tai;Liu, Xue-Wei;
Journal Chemistry, an Asian journal
Year 2019
DOI
10.1002/asia.201900844
URL
Keywords
carbohydrates cascade reaction cyclization fused-ring system rearrangement

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