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

Iioka Ryoya | Zendy; Yorozu Kohei | Zendy; Sakai Yoko | Zendy; Kawai Rika | Zendy; Hatae Noriyuki | Zendy; Takashima Katsuki | Zendy; Tanabe Genzoh | Zendy; Wasada Hiroaki | Zendy; Yoshimatsu Mitsuhiro | Zendy

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

Author(s) -

Iioka Ryoya,

Yorozu Kohei,

Sakai Yoko,

Kawai Rika,

Hatae Noriyuki,

Takashima Katsuki,

Tanabe Genzoh,

Wasada Hiroaki,

Yoshimatsu Mitsuhiro

Publication year - 2021

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202100021

Subject(s) - chemistry , annulation , reagent , indole test , aryl , propargyl , alkyl , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis

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.

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