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叠氮鏻盐导向的（±）-肉桂基-1-三唑的化学选择性合成以及从森田-贝利斯-希尔曼加合物区域选择性合成溴甲基香豆素。

Azidophosphonium salt-directed chemoselective synthesis of ()/()-cinnamyl-1-triazoles and regiospecific access to bromomethylcoumarins from Morita-Baylis-Hillman adducts.

作者信息

Karthikeyan Soundararajan, Shobana Radha Krishnan, Subimol Kamarajapurathu Raju, Monica J Helen Ratna, Kumar Ayyanoth Karthik Krishna

机构信息

Organic & Material Chemistry Research Laboratory, Department of Chemistry, The American College, Madurai, Tamil Nadu, India.

Department of Chemistry, Fatima College, Madurai, Tamil Nadu, India.

出版信息

Beilstein J Org Chem. 2020 Jul 1;16:1579-1587. doi: 10.3762/bjoc.16.130. eCollection 2020.

DOI:10.3762/bjoc.16.130
PMID:32704324
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7356223/
Abstract

The direct transformation of Morita-Baylis-Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding ()/()-cinnamyl-1-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools.

摘要

将森田-贝利斯-希尔曼（MBH）加合物直接转化为目标分子是一个关键过程，其中烯丙基羟基保护的或卤代的MBH加合物通常更受青睐。在此，我们报道了一种叠氮鏻盐（AzPS）催化的直接方法，用于从MBH加合物合成结构复杂的（）/（）-肉桂基-1,2,3-三唑和卤甲基香豆素。这种新颖的方法、高效的催化剂以及在温和反应条件下对MBH加合物的直接利用，使所报道的方法成为强大的合成工具。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/b2e592af6637/Beilstein_J_Org_Chem-16-1579-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/2aa03f905136/Beilstein_J_Org_Chem-16-1579-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/82c7853e7879/Beilstein_J_Org_Chem-16-1579-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/2b3e20c4cd9c/Beilstein_J_Org_Chem-16-1579-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/4fea136fceae/Beilstein_J_Org_Chem-16-1579-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/3f31677aeba8/Beilstein_J_Org_Chem-16-1579-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/b2e592af6637/Beilstein_J_Org_Chem-16-1579-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/2aa03f905136/Beilstein_J_Org_Chem-16-1579-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/82c7853e7879/Beilstein_J_Org_Chem-16-1579-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/2b3e20c4cd9c/Beilstein_J_Org_Chem-16-1579-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/4fea136fceae/Beilstein_J_Org_Chem-16-1579-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/3f31677aeba8/Beilstein_J_Org_Chem-16-1579-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65af/7356223/b2e592af6637/Beilstein_J_Org_Chem-16-1579-g003.jpg

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