CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 108-113
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

Marziyeh Saeedi
a  Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Maryam Khoshdoun
a  Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Salman Taheri
a  Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
b  Faculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran
c  Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104 Freiburg im Breisgau, Germany
,
Aliasghar Mohammadi
a  Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Mohammad Reza Halvagar
a  Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Vahid Amani
d  Department of Chemistry, Farhangian University, Tehran, Iran
› Author Affiliations
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.

Supporting Information



Publication History

Received: 19 March 2021

Accepted after revision: 26 April 2021

Publication Date:
27 April 2021 (online)

© 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/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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