期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 5, 页码 3059-3070出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02953
关键词
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资金
- National Natural Science Foundation of China [21562005]
- Natural Science Foundation of Guangxi [2016GXNSFFA380005]
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources [CMEMR2017-A01]
- Ministry of Education of China [IRT_16R15]
- Overseas 100 Talents Program of Guangxi Higher Education
- One Thousand Young and Middle -Aged College and University Backbone Teachers Cultivation Program of Guangxi
An approach for the construction of furo[3,2-b]quinolines and furo[2,3-b:4,S-b']diquinolines is developed through a metal-free [4 + 2] cycloaddition of easily available in situ generated aza-o-quinone methides and furans. The reaction tolerates a wide range of aza-o-quinone methides and substituted furans to afford the corresponding dihydro- or tetrahydrofuroquinolines in good to excellent yields. Mechanistic studies reveal that the reaction involves a concerted [4 + 2] cycloaddition pathway and shows a high regioselectivity of cycloaddition for a furan ring. The present method features mild reaction conditions, dearomatization of furans, high regio- and diastereoselectivity, gram-scalable preparations, and diversity of furoquinolines.
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