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一种高效的无金属和无催化剂的C-S/C-O键形成策略：吡唑共轭硫代酰胺和酰胺的合成。

An efficient metal-free and catalyst-free C-S/C-O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides.

作者信息

Sharma Shubham, Singh Dharmender, Kumar Sunit, Jamra Rahul, Banyal Naveen, Malakar Chandi C, Singh Virender

机构信息

Department of Chemistry, Dr B R Ambedkar National Institute of Technology (NIT) Jalandhar, 144027, Punjab, India.

Central Revenues Control Laboratory, New Delhi-110012, India.

出版信息

Beilstein J Org Chem. 2023 Mar 2;19:231-244. doi: 10.3762/bjoc.19.22. eCollection 2023.

DOI:10.3762/bjoc.19.22
PMID:36895429
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9989676/
Abstract

An operationally simple and metal-free approach is described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The thioamides were generated by employing a three-component reaction of diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, and elemental sulfur in a single synthetic operation. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover, the pyrazole C-3/5-linked amide conjugates were also synthesized via an oxidative amination of pyrazole carbaldehydes and 2-aminopyridines using hydrogen peroxide as an oxidant.

摘要

本文描述了一种操作简单且无金属的方法来合成吡唑连接的硫代酰胺和酰胺共轭物。硫代酰胺是通过在单一合成操作中使用多种吡唑C-3/4/5醛、仲胺和元素硫的三组分反应生成的。该开发方案的优点包括底物范围广、无金属且反应条件易于操作。此外，吡唑C-3/5连接的酰胺共轭物也通过使用过氧化氢作为氧化剂，对吡唑醛和2-氨基吡啶进行氧化胺化反应来合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/13bbbefa47a5/Beilstein_J_Org_Chem-19-231-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/2e38906a8ffc/Beilstein_J_Org_Chem-19-231-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/2e9b764aae08/Beilstein_J_Org_Chem-19-231-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/bc1d0ff05a67/Beilstein_J_Org_Chem-19-231-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/f26ef12f6dbe/Beilstein_J_Org_Chem-19-231-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/98e8811af71e/Beilstein_J_Org_Chem-19-231-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/33c39180c2b8/Beilstein_J_Org_Chem-19-231-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/d39c9992ea7a/Beilstein_J_Org_Chem-19-231-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/54c58f213fa7/Beilstein_J_Org_Chem-19-231-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/9ec333e57edc/Beilstein_J_Org_Chem-19-231-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/c927bb8f2717/Beilstein_J_Org_Chem-19-231-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/13bbbefa47a5/Beilstein_J_Org_Chem-19-231-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/2e38906a8ffc/Beilstein_J_Org_Chem-19-231-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/2e9b764aae08/Beilstein_J_Org_Chem-19-231-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/bc1d0ff05a67/Beilstein_J_Org_Chem-19-231-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/f26ef12f6dbe/Beilstein_J_Org_Chem-19-231-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/98e8811af71e/Beilstein_J_Org_Chem-19-231-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/33c39180c2b8/Beilstein_J_Org_Chem-19-231-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/d39c9992ea7a/Beilstein_J_Org_Chem-19-231-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/54c58f213fa7/Beilstein_J_Org_Chem-19-231-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/9ec333e57edc/Beilstein_J_Org_Chem-19-231-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/c927bb8f2717/Beilstein_J_Org_Chem-19-231-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/40f9/9989676/13bbbefa47a5/Beilstein_J_Org_Chem-19-231-g012.jpg

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