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6-氨基-2-氰基苯并噻唑的经济且可扩展的合成

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole.

作者信息

Hauser Jacob R, Beard Hester A, Bayana Mary E, Jolley Katherine E, Warriner Stuart L, Bon Robin S

机构信息

School of Chemistry, University of Leeds; Astbury Centre for Structural Molecular Biology.

School of Chemistry, University of Leeds; Institute of Process Research and Development.

出版信息

Beilstein J Org Chem. 2016 Sep 13;12:2019-2025. doi: 10.3762/bjoc.12.189. eCollection 2016.

DOI:10.3762/bjoc.12.189
PMID:27829906
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5082452/
Abstract

2-Cyanobenzothiazoles (CBTs) are useful building blocks for: 1) luciferin derivatives for bioluminescent imaging; and 2) handles for bioorthogonal ligations. A particularly versatile CBT is 6-amino-2-cyanobenzothiazole (ACBT), which has an amine handle for straight-forward derivatisation. Here we present an economical and scalable synthesis of ACBT based on a cyanation catalysed by 1,4-diazabicyclo[2.2.2]octane (DABCO), and discuss its advantages for scale-up over previously reported routes.

摘要

2-氰基苯并噻唑（CBTs）是用于以下方面的有用构建模块：1）用于生物发光成像的萤光素衍生物；2）生物正交连接的连接基团。一种特别通用的CBT是6-氨基-2-氰基苯并噻唑（ACBT），它具有一个便于直接衍生化的胺基连接基团。在此，我们展示了一种基于1,4-二氮杂双环[2.2.2]辛烷（DABCO）催化的氰化反应的ACBT经济且可扩展的合成方法，并讨论了其相对于先前报道的路线在放大生产方面的优势。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/6e61d9860394/Beilstein_J_Org_Chem-12-2019-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/19a33003fb2f/Beilstein_J_Org_Chem-12-2019-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/e0ed22341a99/Beilstein_J_Org_Chem-12-2019-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/965982419070/Beilstein_J_Org_Chem-12-2019-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/6e61d9860394/Beilstein_J_Org_Chem-12-2019-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/19a33003fb2f/Beilstein_J_Org_Chem-12-2019-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/e0ed22341a99/Beilstein_J_Org_Chem-12-2019-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/965982419070/Beilstein_J_Org_Chem-12-2019-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b1c/5082452/6e61d9860394/Beilstein_J_Org_Chem-12-2019-g005.jpg

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