Diverse privileged N-polycyclic skeletons accessed from a metal-free cascade cyclization reaction. Issue 37 (3rd September 2021)

• Record Type: Journal Article
• Authors: Li, Wenzhong; Wang, Yu; Qi, Huijing; Shi, Ran; Li, Jiazhu; Chen, Si; Xu, Xin-Ming; Wang, Wei-Li
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 37(2021)
• Page Start: 8086
• Page End: 8095
• Publication Date: 2021-09-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01206a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Metal-free cascade cyclization of 2-acylbenzoic acids with amines provided a one-pot synthesis of diverse isoindoloisoquinoline and benzoindolizinoindole derivatives, which were subsequently used to produce nitrogen-containing nine-membered ring compounds. Abstract : An exquisite metal-free cascade cyclization reaction of 2-acylbenzoic acids with amines was developed, which provided a powerful method for the one-pot synthesis of diverse isoindoloisoquinoline and benzoindolizinoindole derivatives. This protocol avoided the use of metal catalysts, proceeded with high efficiency and had broad substrate scope. These resulting products could be transformed into tertiary amines under the reduction of LiAlH4 /AlCl3, followed by the Hofmann elimination offering lots of nitrogen-containing nine-membered ring compounds in excellent yields. All synthesized products containing fused N -polycyclic skeletons were difficult to be constructed using traditional methods and they have a wide range of applications in the pharmaceutical area.