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微波辅助由4-氨基丁醇合成2-取代的4,5,6,7-四氢-1,3-噻氮杂环庚烷。

Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol.

作者信息

Mollo María C, Kilimciler Natalia B, Bisceglia Juan A, Orelli Liliana R

机构信息

Universidad de Buenos Aires. CONICET. Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica. Junín 956, (1113) Buenos Aires, Argentina.

出版信息

Beilstein J Org Chem. 2020 Jan 6;16:32-38. doi: 10.3762/bjoc.16.5. eCollection 2020.

DOI:10.3762/bjoc.16.5
PMID:31976014
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6964664/
Abstract

A general procedure for the synthesis of 2-substituted tetrahydro-1,3-thiazepines by MW-assisted cyclization of 4-thioamidobutanols is presented. The acyclic precursors were prepared in high overall yields by an expeditious three-step diacylation/thionation/deprotection sequence from 4-aminobutanol. Microwave-assisted ring closure of 4-thioamido alcohols promoted by trimethylsilyl polyphosphate (PPSE) in solvent-free conditions allowed for the synthesis of several hitherto unreported seven-membered iminothioethers bearing 2-aryl, alkenyl, aralkyl and alkyl substituents. The cyclodehydration reaction is likely to involve an S2-type displacement and affords good to excellent yields of the desired heterocycles in very short reaction times.

摘要

本文介绍了一种通过微波辅助4-硫代氨基丁醇环化反应合成2-取代四氢-1,3-硫氮杂卓的通用方法。通过从4-氨基丁醇开始的快速三步二酰化/硫代化/脱保护序列，以较高的总收率制备了无环前体。在无溶剂条件下，由三甲基甲硅烷基多磷酸酯（PPSE）促进的4-硫代氨基醇的微波辅助闭环反应，能够合成几种迄今未报道的带有2-芳基、烯基、芳烷基和烷基取代基的七元亚氨基硫醚。环脱水反应可能涉及S2型取代，并在非常短的反应时间内以良好到优异的产率得到所需的杂环化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/df1f/6964664/c8e98b5fb326/Beilstein_J_Org_Chem-16-32-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/df1f/6964664/0ef97cc4addb/Beilstein_J_Org_Chem-16-32-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/df1f/6964664/c8e98b5fb326/Beilstein_J_Org_Chem-16-32-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/df1f/6964664/0ef97cc4addb/Beilstein_J_Org_Chem-16-32-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/df1f/6964664/c8e98b5fb326/Beilstein_J_Org_Chem-16-32-g003.jpg

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本文引用的文献

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