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通过 2-叠氮苯甲醛与苯硒腈的双环化反应合成 4-(苯硒基)四唑并[1,5-a]喹啉。

Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile.

机构信息

Laboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, Pelotas 96010-900, RS, Brazil.

Departamento de Química, Universidade Federal de Santa Maria-UFSM, Av. Roraima, Building 18, Santa Maria 97105-900, RS, Brazil.

出版信息

Molecules. 2023 Jun 27;28(13):5036. doi: 10.3390/molecules28135036.

DOI:10.3390/molecules28135036
PMID:37446698
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10343424/
Abstract

A general methodology to access valuable 4-(phenylchalcogenyl)tetrazolo[1,5-]quinolines was developed by the reaction of 2-azidobenzaldehyde with phenylchalcogenylacetonitriles (sulfur and selenium) in the presence of potassium carbonate (20 mol%) as a catalyst. The reactions were conducted using a mixture of dimethylsulfoxide and water (7:3) as solvent at 80 °C for 4 h. This new methodology presents a good functional group tolerance to electron-deficient and electron-rich substituents, affording a total of twelve different 4-(phenylchalcogenyl)tetrazolo[1,5-]quinolines selectively in moderate to excellent yields. The structure of the synthesized 4-(phenylselanyl)tetrazolo[1,5-]quinoline was confirmed by X-ray analysis.

摘要

开发了一种通用方法，通过 2-叠氮苯甲醛与苯硒腈（硫和硒）在碳酸钾（20mol%）作为催化剂的存在下反应，可获得有价值的 4-（苯基硒基）四唑并[1,5-a]喹啉。反应在二甲基亚砜和水（7：3）的混合物中，在 80°C 下进行 4 小时。该新方法对缺电子和富电子取代基具有良好的官能团耐受性，以中等至优异的收率选择性地得到了总共 12 种不同的 4-（苯基硒基）四唑并[1,5-a]喹啉。通过 X 射线分析证实了合成的 4-（苯硒基）四唑并[1,5-a]喹啉的结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/7618d799af1f/molecules-28-05036-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/8d6093d06319/molecules-28-05036-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/3f2e3a01c10c/molecules-28-05036-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/f52ceed065d8/molecules-28-05036-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/828ea03c769e/molecules-28-05036-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/7af75edaf4e0/molecules-28-05036-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/f812a135ec49/molecules-28-05036-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/7618d799af1f/molecules-28-05036-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/8d6093d06319/molecules-28-05036-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/3f2e3a01c10c/molecules-28-05036-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/f52ceed065d8/molecules-28-05036-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/828ea03c769e/molecules-28-05036-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/7af75edaf4e0/molecules-28-05036-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/f812a135ec49/molecules-28-05036-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0623/10343424/7618d799af1f/molecules-28-05036-sch005.jpg

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