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분자분광학및동력학연구단
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Efficient and Inexpensive Synthesis of 15N-Labeled 2-Azido-1,3-dimethylimidazolinium Salts Using Na15NO2 Instead of Na15NNN

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Title
Efficient and Inexpensive Synthesis of <sup>15</sup>N-Labeled 2-Azido-1,3-dimethylimidazolinium Salts Using Na<sup>15</sup>NO<sub>2</sub> Instead of Na<sup>15</sup>NNN
Author(s)
Gwak, Sungduk; Jun Young Park; Minhaeng Cho; Kwon, Hyeok-Jun; Han, Hogyu
Publication Date
2024-02
Journal
ACS Omega, v.9, no.6, pp.6556 - 6560
Publisher
ACS Publications
Abstract
N-15-Labeled azides are important probes for infrared and magnetic resonance spectroscopy and imaging. They can be synthesized by reaction of primary amines with a N-15-labeled diazo-transfer reagent. We present the synthesis of N-15-labeled 2-azido-1,3-dimethylimidazolinium salts 1 as a N-15-labeled diazo-transfer reagent. Nitrosation of 1,3-dimethylimidazolinium-2-yl hydrazine (2) with (NaNO2)-N-15 under acidic conditions gave 1 as a 1:1 mixture of alpha- and gamma-N-15-labeled azides, alpha- and gamma-1, rather than gamma-1 alone. The isotopomeric mixture thus obtained was then subjected to the diazo-transfer reaction with primary amines 3 to afford azides 4 as a 1:1 mixture of beta-N-15-labeled azides beta-4 and unlabeled ones 4'. The efficient and inexpensive synthesis of 1 as a 1:1 mixture of alpha- and gamma-1 using (NaNO2)-N-15 instead of (NaNNN)-N-15 facilitates their wide use as a N-15-labeled diazo-transfer reagent for preparing N-15-labeled azides as molecular probes.
URI
https://pr.ibs.re.kr/handle/8788114/14858
DOI
10.1021/acsomega.3c07147
Appears in Collections:
Center for Molecular Spectroscopy and Dynamics(분자 분광학 및 동력학 연구단) > 1. Journal Papers (저널논문)
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