期刊
ACS COMBINATORIAL SCIENCE
卷 17, 期 8, 页码 474-481出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.5b00065
关键词
multicomponent reaction (MCR); Ugi reaction; U4CC; ipso-iodocyclization; Suzuki coupling; Spiro compounds
资金
- CSIR, New Delhi under THUNDER [BSC-0102]
- CSIR, New Delhi under ACT [CSC0301]
- UGC, New Delhi
A solution-phase parallel synthesis of pharmaceutically important azaspiro[4.5]trienones has been developed by performing tandem Ugi four-component condensation (U4CC), involving substituted p-anisidines, aldehydes, 3-alkyl/aryl-propiolic acids, and isocyanides, and iodine-mediated ipso-iodocyclization in one-pot. This highly atom economical process produced functionalized azaspiro[4.5]trienones in good to excellent overall yields and products were easily isolated by precipitation followed by crystallization. These vinyl-iodide bearing azaspiro[4.5]trienones were utilized for further modifications through Suzuki coupling and deiodination reaction to demonstrate the suitability of these products for various palladium catalyzed modifications. The present method provides an easy access to highly functionalized azaspiro[4.5]trienones that can be useful in drug discovery research.
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