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CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 108-113
DOI: 10.1055/a-1492-9229
DOI: 10.1055/a-1492-9229
paper
Virtual Collection in Honor of Prof. Issa Yavari
Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal
We thank the Research Council of the Chemistry and Chemical Engineering Research Center of Iran (CCERCI) and the Faculty of Chemistry of Kharazmi University for supporting this work. A.Z.H. thanks the Alexander von Humboldt-Stiftung for supporting his research in the Albert-Ludwigs-Universität Freiburg.
Abstract
An efficient method for the synthesis of highly substituted bicyclic pyridone derivatives containing the dithiocarbamate group is reported via a one-pot three-component reaction of 2-(alkylthio)thioazlactones, diamines, and nitroketene dithioacetal in EtOH under catalyst-free conditions. The reaction proceeds via a domino amidation–intramolecular 1,4-addition-type Friedel–Crafts alkylation reaction to afford the corresponding fused bicyclic pyridones with high yields and diastereoselectivity.
Key words
thioazlactone - nitroketene dithioacetal - bicyclic pyridine - dithiocarbamate - catalyst-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1492-9229.
- Supporting Information
Publication History
Received: 19 March 2021
Accepted after revision: 26 April 2021
Accepted Manuscript online:
27 April 2021
Article published online:
11 May 2021
© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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