Synthesis of Azepino[1,2‐a]indole‐10‐amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent

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 int...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-03, Vol.2021 (10), p.1553-1558
Main Authors: Iioka, Ryoya, Yorozu, Kohei, Sakai, Yoko, Kawai, Rika, Hatae, Noriyuki, Takashima, Katsuki, Tanabe, Genzoh, Wasada, Hiroaki, Yoshimatsu, Mitsuhiro
Format: Article
Language:English
Subjects:
Annulation
Antitumor agents
Scandium
Zinc
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Summary: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. 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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100021