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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

Authors :
Soundararajan Karthikeyan
Radha Krishnan Shobana
Kamarajapurathu Raju Subimol
J. Helen Ratna Monica
Ayyanoth Karthik Krishna Kumar
Source :
Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 1579-1587 (2020)
Publication Year :
2020
Publisher :
Beilstein-Institut, 2020.

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 (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.

Details

Language :
English
ISSN :
18605397
Volume :
16
Issue :
1
Database :
Directory of Open Access Journals
Journal :
Beilstein Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.90f3a4a22b5848deb64907eb8ca74fe6
Document Type :
article
Full Text :
https://doi.org/10.3762/bjoc.16.130