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硝酸铋促进的 1-取代-5-氨基四唑的三组分合成

Three-Component Synthesis of 1-Substituted 5-Aminotetrazoles Promoted by Bismuth Nitrate.

作者信息

de Jesus Iva S, Trindade Gomes Amenson, Sande Igor, Cunha Silvio

机构信息

Instituto de Química, Universidade Federal da Bahia, Campus de Ondina, Salvador, Bahia 40170-115, Brazil.

Instituto Nacional de Ciência e Tecnologia - INCT em Energia e Ambiente, Campus Ondina, Salvador, Bahia 40170-290, Brazil.

出版信息

J Org Chem. 2024 Oct 4;89(19):14279-14290. doi: 10.1021/acs.joc.4c01727. Epub 2024 Sep 13.

DOI:10.1021/acs.joc.4c01727
PMID:39269756
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11459472/
Abstract

A nontoxic bismuth-promoted multicomponent synthesis of 5-aminotetrazoles and bistetrazoles is reported. The reaction of phenyl isothiocyanate, NaN, and amine (primary aliphatic, aromatic, and aliphatic diamine) promoted by Bi(NO)·5HO under microwave heating affords good yields, short reaction times, simple workup, and purification without column chromatography. A set of diagnostic H NMR signals was identified as a guide for quickly elucidating the exclusive (or main) regioisomer formed, with the stronger electron donor group located at heterocyclic nitrogen 1. This regioselectivity is strongly dependent on the electronic density of the amine. It is opposite to that obtained by several thiourea desulfurization methods promoted by thiophilic metals and metal-free protocols.

摘要

报道了一种由无毒铋促进的5-氨基四唑和双四唑的多组分合成方法。在微波加热条件下，由Bi(NO₃)₃·5H₂O促进的苯基异硫氰酸酯、NaN₃和胺（脂肪族伯胺、芳香胺和脂肪族二胺）的反应，产率高、反应时间短、后处理简单，无需柱色谱法进行纯化。一组诊断性的¹H NMR信号被确定为快速阐明所形成的唯一（或主要）区域异构体的指南，较强的供电子基团位于杂环氮1处。这种区域选择性强烈依赖于胺的电子密度。它与通过亲硫金属促进的几种硫脲脱硫方法和无金属方案所获得的结果相反。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/bfbd097e00a3/jo4c01727_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/30bc8a0464c0/jo4c01727_0001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/d4605318e7d7/jo4c01727_0005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/e0d11b101124/jo4c01727_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/d164fa4412ba/jo4c01727_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/bfbd097e00a3/jo4c01727_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/30bc8a0464c0/jo4c01727_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/7d93e4bd71c3/jo4c01727_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/8bd07afd0b2a/jo4c01727_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/d4605318e7d7/jo4c01727_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/4bad2ebaafe6/jo4c01727_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/e0d11b101124/jo4c01727_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/d164fa4412ba/jo4c01727_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ea8/11459472/bfbd097e00a3/jo4c01727_0008.jpg

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