Diastereoselective synthesis of 3, 3-disubstituted 3-nitro-4-chromanone derivatives as potential antitumor agents. Issue 5 (14th January 2019)

• Record Type: Journal Article
• Authors: Chen, Huiqing; Xie, Jia; Xing, Dong; Wang, Jinping; Tang, Jie; Yi, Zhengfang; Xia, Fei; Qiu, Wen-Wei; Yang, Fan
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 5(2019)
• Page Start: 1062
• Page End: 1066
• Publication Date: 2019-01-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02761g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We report an efficient and highly diastereoselective protocol for the rapid construction of 3-nitro substituted 4-chromanones by an intramolecular Michael-type cyclization of α-nitro aryl ketones bearing unsaturated ester units. Abstract : We report an efficient and highly diastereoselective protocol for the rapid construction of 3-nitro substituted 4-chromanones by an intramolecular Michael-type cyclization of α-nitro aryl ketones bearing unsaturated ester units. A catalytic amount of KO t Bu was found to be crucial for the high diastereoselective control of this transformation. With this protocol, a series of 3, 3-disubstituted 3-nitro-4-chromanones were synthesized in good to excellent yields with high diastereoselectivities and showed moderate to good in vitro antitumor activities, representing promising antitumor hits for further drug discovery.