Topic
Triazene
About: Triazene is a research topic. Over the lifetime, 759 publications have been published within this topic receiving 8714 citations. The topic is also known as: Triazene cleavage & 1-triazene.
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01 Jan 2012
TL;DR: In this paper, a new approach to benzylamines using triazene compounds has been developed that is facilitated by the lithiation of aryltriazenes followed by treatment with an electrophile.
Abstract: A new approach to benzylamines using triazene compounds has been developed that is facilitated by the lithiation of aryltriazenes followed by treatment with an electrophile The regioselectivity of the reaction can be controlled by means of the substituents in the aryl group The reaction contains the following steps: intramolecular carbon–carbon bond formation involving lithiation of an alkyl group on a 3-nitrogen atom; a 1,2-proton shift; and the subsequent release of nitrogen gas Through the use of a deuterated triazene, we were able to determine that the reaction proceeds through a 1,2-proton shift
TL;DR: Alkyl, benzyl, aryl, and hetaryl carboxylic acids are successfully coupled with primary aliphatic and aromatic amines as well as secondary aliphastic amines as mentioned in this paper.
Abstract: Alkyl, benzyl, aryl, and hetaryl carboxylic acids are successfully coupled with primary aliphatic and aromatic amines as well as secondary aliphatic amines.
TL;DR: The 1,3-diaza-2-azoniaallene salt 3a reacts stereoselectively with glycals (5a,b) to afford pyrano[2, 3-d]-1, 2, 3 -triazolium salts as discussed by the authors.
Abstract: The 1,3-diaza-2-azoniaallene salt 3a reacts stereoselectively with glycals (5a—e) to afford pyrano[2,3-d]-1,2,3- triazolium salts 6a—e. In contrast to other 1,3-dipolar cycloadditions of glycals reported so far, the stereoselectivity of compounds 6 is not determined by the substituent on C-3 of the glycal. Both cis (6a,b) and trans (6d,e) substitutions on C-7 and C-7a were found for bicyclic compounds 6 (crystal structure of 6a). Under the influence of acid 6e opens the pyran ring to give the triazolium salt 9. Addition of antimony pentachloride to a solution of the glycal 5e and the chlorotriazene 2a results in the formation of the pyranotriazene 12 containing two triazene units. In the presence of acid the pyranotriazene 6c reacts with alcohols to afford 2-hydrazino glycosides 13a,b, 15, which with zinc dust in acetic acid are reduced to 2-amino glycosides 14a,b.