Issue 13, 2013
From the journal:

Organic & Biomolecular Chemistry

A three-component reaction of C,N-cyclic N′-acyl azomethineimines, isocyanides, and azide compounds: effective synthesis of 1,5-disubstituted tetrazoles with tetrahydroisoquinoline skeletons†

Takahiro Soeta,*a   Kaname Tamura,a   Shuhei Fujinamia  and  Yutaka Ukaji*a  

* Corresponding authors

a Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan
E-mail: soeta@se.kanazawa-u.ac.jp, ukaji@staff.kanazawa-u.ac.jp

Abstract

A multicomponent reaction of isocyanides and C,N-cyclic N′-acyl azomethine imines in the presence of TMSCl and NaN3 leads to tetrazole derivatives. These reactions proceeded cleanly to afford the corresponding 1,5-disubstituted tetrazoles containing a tetrahydroisoquinoline skeleton in high to excellent yields.

Graphical abstract: A three-component reaction of C,N-cyclic N′-acyl azomethine imines, isocyanides, and azide compounds: effective synthesis of 1,5-disubstituted tetrazoles with tetrahydroisoquinoline skeletons

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Article information

DOI
https://doi.org/10.1039/C3OB27297D
Article type
Paper
Submitted
27 Nov 2012
Accepted
29 Jan 2013
First published
30 Jan 2013

Org. Biomol. Chem., 2013,11, 2168-2174

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A three-component reaction of C,N-cyclic N′-acyl azomethine imines, isocyanides, and azide compounds: effective synthesis of 1,5-disubstituted tetrazoles with tetrahydroisoquinoline skeletons

T. Soeta, K. Tamura, S. Fujinami and Y. Ukaji, Org. Biomol. Chem., 2013, 11, 2168 DOI: 10.1039/C3OB27297D

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