ArticleThe Journal of organic chemistry2014
A Lewis Acid Catalyzed annulation to 2,1-benzisoxazoles.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- One-Pot Synthesis of Benzoxazoles: A Promising Approach to Aromatic Heterocyclic Compounds Preparation.Medicinal chemistry (Shariqah (United Arab Emirates)) · 2025Review
- Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids.The Journal of organic chemistry · 2016Article
- Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids.Beilstein journal of organic chemistry · 2016Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
We report here a new, atom economical annulation to 2,1-benzisoxazole scaffolds via the BF3·Et2O-catalyzed reaction of glyoxylate esters and nitrosoarenes. The developed method represents a convergent route to this compound class from previously unexplored inputs and provides a range of 2,1-benzisoxazoles in moderate to high yields under convenient conditions. Along with exploration of substrate scope, initial mechanistic investigation through (18)O labeling and the synthesis of a reaction intermediate provides evidence for an unusual umpolung addition of glyoxylates to nitrosobenzenes with high O-selectivity, followed by a new type of Friedel-Crafts cyclization.
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