Synthesis of Azepino[1, 2‐a]indole‐10‐amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent. Issue 10 (16th February 2021)

• Record Type: Journal Article
• Authors: Iioka, Ryoya; Yorozu, Kohei; Sakai, Yoko; Kawai, Rika; Hatae, Noriyuki; Takashima, Katsuki; Tanabe, Genzoh; Wasada, Hiroaki; Yoshimatsu, Mitsuhiro
• Is Part Of: European journal of organic chemistry. Issue 10(2021)
• Page Start: 1553
• Page End: 1558
• Publication Date: 2021-02-16
• Subjects: Annulation -- Antitumor agents -- Scandium -- Zinc; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100021
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Lewis acid‐catalyzed [6+1] annulation reactions of 2‐cyano‐1‐propargyl‐ and 2‐alkynyl‐1‐cyanomethyl‐indoles with Reformatsky reagent are described. 8‐Aryl, 8‐alkyl‐, 8‐hetaryl‐, 9‐aryl, and 9‐alkyl‐azepino[1, 2‐a]indole amines were obtained through a 7‐endo‐mode cyclization of the β‐aminoacrylate intermediates. The antiproliferative activity of the azepino[1, 2‐a]indoles analogs against the HCT‐116 cells were also examined. Abstract : Scandium‐ or hafnium‐catalyzed [6+1] annulation reactions of 2‐cyano‐1‐propargyl‐ and 2‐alkynyl‐1‐cyanomethyl‐indoles with Reformatsky reagent delivered 8‐ and 9‐substituted‐azepino[1, 2‐a]indole amines in good to high yields.