دورية أكاديمية

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

التفاصيل البيبلوغرافية
العنوان: 1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles
المؤلفون: Tomas Opsomer, Kaat Valkeneers, Ana Ratković, Wim Dehaen
المصدر: Organics, Vol 2, Iss 4, Pp 404-414 (2021)
بيانات النشر: MDPI AG, 2021.
سنة النشر: 2021
المجموعة: LCC:Organic chemistry
مصطلحات موضوعية: 1,2,3-triazole, aldehyde, cycloaddition, enamine, Cornforth, rearrangement, Organic chemistry, QD241-441
الوصف: 1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.
نوع الوثيقة: article
وصف الملف: electronic resource
اللغة: English
تدمد: 2673-401X
Relation: https://www.mdpi.com/2673-401X/2/4/24; https://doaj.org/toc/2673-401X
DOI: 10.3390/org2040024
URL الوصول: https://doaj.org/article/323963ff568b4845be5823eb7d677265
رقم الأكسشن: edsdoj.323963ff568b4845be5823eb7d677265
قاعدة البيانات: Directory of Open Access Journals
الوصف
تدمد:2673401X
DOI:10.3390/org2040024