Six‐Component Azido‐Ugi Reaction: from Cyclic Ketimines to Bis‐Tetrazole‐Derived 5–7‐Membered Amines

A new six‐component azido‐Ugi reaction was investigated. Using cyclic ketimines as starting materials highly efficient, synthesis of 5‐, 6‐ and 7‐membered cyclic amines connected with two tetrazole rings was elaborated. The influence of different components (ketimine, aldehyde, isocyanide) on the re...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2019-04, Vol.2019 (15), p.2675-2681
Main Authors: Kutovaya, Irina V., Zarezin, Danil P., Shmatova, Olga I., Nenajdenko, Valentine G.
Format: Article
Language:English
Subjects:
Amines
Hydrogenolysis
Imines
Multicomponent reactions
Nitrogen heterocycles
Tetrazole
Tetrazoles
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new six‐component azido‐Ugi reaction was investigated. Using cyclic ketimines as starting materials highly efficient, synthesis of 5‐, 6‐ and 7‐membered cyclic amines connected with two tetrazole rings was elaborated. The influence of different components (ketimine, aldehyde, isocyanide) on the reaction was studied. It was demonstrated that bis‐tetrazoles derived from benzyl isocyanide can be converted efficiently to NH‐tetrazoles by hydrogenolysis. The six‐component azido‐Ugi reaction with 2‐substituted 5–7‐membered imines leads to mono‐ or bis‐tetrazole derivatives depending on the starting imines. The reaction is very general regarding isocyanide structure and enables preparation of 1,5‐disubstituted bis‐tetrazole derivatives connected with 5–7‐membered cyclic amine fragments. Subsequent catalytic debenzylation provides the corresponding 1H‐tetrazoles.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900244