Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 51, Pages 8002-8005Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc02659a
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Funding
- National Natural Science Foundation of China [21402070]
- Personnel Training Foundation of Kunming University of Science and Technology [14118841]
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Divergent cascade syntheses constitute a highly attractive and challenging area in synthetic chemistry, and can exhibit unexpected chemoselectivity. Herein, a Bronsted acid-controlled protocol is described for the efficient catalysis of two different reactions, namely acylation cascade- and [1+2+3]-type cyclization of enaminones and isatins for the concise synthesis of highly functionalized pyrrolo[3,4-c]quinolin-1-ones and spirooxindoles in the presence of carboxylic acids and KHSO4, respectively. The observed chemoselectivity was reasonably explained by trapping the intermediate alpha,beta-unsaturated 2-oxindoles, and the source of the hydroxyl group, carbocation intermediate, and amination reaction were also evaluated.
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