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Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita-Baylis-Hillman adducts.
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-07-01 , DOI: 10.3762/bjoc.16.130
Soundararajan Karthikeyan 1 , Radha Krishnan Shobana 1 , Kamarajapurathu Raju Subimol 2 , J Helen Ratna Monica 1 , Ayyanoth Karthik Krishna Kumar 1
Affiliation  

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 (E)/(Z)-cinnamyl-1H-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.

中文翻译:

(E)/(Z)-肉桂基-1H-三唑以叠氮phosph盐为导向的化学选择性合成反应,以及从Morita-Baylis-Hillman加合物获得溴甲基香豆素的区域特异性通道。

Morita-Baylis-Hillman(MBH)加合物直接转化为目标分子是关键过程,其中通常首选烯丙基羟基保护或卤代MBH加合物。在这里,我们报告了叠氮phosph盐(AzPS)催化的直接协议,用于从MBH加合物合成结构上苛刻的(E)/(Z)-肉桂基-1 H -1,2,3-三唑和卤代甲基香豆素。新颖的方法,高效的催化剂以及在温和的反应条件下直接利用MBH加合物,使所报导的方法成为强大的合成工具。
更新日期:2020-07-01
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