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5-Alkylamino-1H-1,2,3-triazoles by Base-Mediated Cleavage of Cycloadducts of Azides to Cyclic Ketene N,N-Acetals.

✍ Scribed by Helmut Quast; Manfred Ach; Thomas Hergenroether; Dieter Regnat

Publisher
John Wiley and Sons
Year
2006
Weight
20 KB
Volume
37
Category
Article
ISSN
0931-7597

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✦ Synopsis

Abstract

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Triazenes by Acid-Mediated Opening of th
Triazenes by Acid-Mediated Opening of the Dihydro-1,2,3-triazole Ring of1,3-Dipolar Cycloadducts of Organic Azides to Cyclic Ketene N,N-Acetals
✍ Helmut Quast; Manfred Ach; Dieter Regnat 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 English ⚖ 194 KB

## Abstract Spirocyclic 1,3‐dipolar cycloadducts **1** and **4** of azides to heterocyclic ketene N,N‐acetals open their dihydro‐1,2,3‐triazole ring in the presence of weak Brønsted acids to afford novel 1,3‐substituted triazenes **2**X and **5**X, respectively, which form colorless, crystallized t

Exploring the Border between Concerted a
Exploring the Border between Concerted and Two-Step Pathways of 1,3-Dipolar Cycloadditions of Organic Azides to Cyclic Ketene N,X-Acetals. – Synthesis and 15N-NMR Spectra of Zwitterions and Spirocyclic Cycloadducts
✍ Helmut Quast; Manfred Ach; Jürgen Balthasar; Thomas Hergenröther; Dieter Regnat; 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 German ⚖ 268 KB

## Abstract Cyclic ketene N,X‐acetals 1 are electron‐rich dipolarophiles that undergo 1,3‐dipolar cycloaddition reactions with organic azides 2 ranging from alkyl to strongly electron‐deficient azides, __e.g.__, picryl azide (2L; R^1^=2,4,6‐(NO~2~)~3~C~6~H~2~) and sulfonyl azides 2M–O (R^1^=XSO~2~;