Brønsted‐Acid‐Catalyzed Substrate‐Controlled and Site‐Selective Friedel–Crafts Alkylation: A New Strategy for Post‐Modification of 1, 2‐Dihydroquinolines. Issue 12 (18th October 2017)

• Record Type: Journal Article
• Authors: Huang, Jin; Li, Guangxun; Yang, Guobin; Zhao, Jinzhong; Tang, Zhuo
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 12(2017)
• Page Start: 1741
• Page End: 1744
• Publication Date: 2017-10-18
• Subjects: alkylation -- asymmetric catalysis -- enantioselectivity -- regioselectivity -- synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700438
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A variety of C3‐, C6‐, C8‐ and C13‐functionalized 1, 2‐dihidroquinolines (1, 2‐DHQs) have been prepared through post‐modification of simple 1, 2‐DHQs by regioselective Friedel–Crafts alkylations. Several commonly used electrophiles such as 3‐indolylmethanol derivatives, nitroolefins, 1, 4‐benzoquinones, aromatic aldehydes and ethoxycarbonyl‐2‐ethoxy‐1, 2‐dihydroquinoline were rationally used to afford the corresponding 1, 2‐DHQs with high yield and regioselectivity. The regioselectivity of the reaction appears to be governed by the substituents of the 1, 2‐DHQ substrates. Abstract : Post‐modifications of simple 1, 2‐dihidroquinolines (1, 2‐DHQs) through regioselective Friedel–Crafts alkylations were achieved using simple Brønsted acid catalysts. Suitable substrates allowed modifications of the specific sites.