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2019•European Journal of Organic ChemistryRequires access

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

Irina V. Kutovaya, Danil P. Zarezin, Olga I. Shmatova, Valentine G. Nenajdenko

Open publisher page 14 citations

Abstract

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.

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What this paper is about

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.

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Available abstract

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.

Key concepts: Isocyanide, Tetrazole, Chemistry, Hydrogenolysis, Ugi reaction, Aldehyde, Component (thermodynamics), Organic chemistry

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Six‐Component Azido‐Ugi Reaction: from Cyclic Ketimines to Bis‐Tetrazole‐Derived 5–7‐Membered Amines — Research Paper | ScholarLens