Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

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 reacti...

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Main Authors: Marziyeh Saeedi, Maryam Khoshdoun, Salman Taheri, Azim Ziyaei Halimehjani, Aliasghar Mohammadi, Mohammad Reza Halvagar, Vahid Amani
Format: Article
Language:English
Published: Georg Thieme Verlag KG 2021-04-01
Series:SynOpen
Subjects:
thioazlactone
nitroketene dithioacetal
bicyclic pyridine
dithiocarbamate
catalyst-free
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/a-1492-9229
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spelling doaj-4ba5abcecf38411994bee92d658787ed2021-05-11T23:49:33ZengGeorg Thieme Verlag KGSynOpen2509-93962021-04-01050210811310.1055/a-1492-9229Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene DithioacetalMarziyeh Saeedi0Maryam Khoshdoun1Salman Taheri2Azim Ziyaei Halimehjani3Aliasghar Mohammadi4Mohammad Reza Halvagar5Vahid Amani6Chemistry & Chemical Engineering Research Center of IranChemistry & Chemical Engineering Research Center of IranChemistry & Chemical Engineering Research Center of IranFaculty of Chemistry, Kharazmi UniversityChemistry & Chemical Engineering Research Center of IranChemistry & Chemical Engineering Research Center of IranDepartment of Chemistry, Farhangian UniversityAn 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.http://www.thieme-connect.de/DOI/DOI?10.1055/a-1492-9229thioazlactonenitroketene dithioacetalbicyclic pyridinedithiocarbamatecatalyst-free
collection DOAJ
language English
format Article
sources DOAJ
author Marziyeh Saeedi
Maryam Khoshdoun
Salman Taheri
Azim Ziyaei Halimehjani
Aliasghar Mohammadi
Mohammad Reza Halvagar
Vahid Amani
spellingShingle Marziyeh Saeedi
Maryam Khoshdoun
Salman Taheri
Azim Ziyaei Halimehjani
Aliasghar Mohammadi
Mohammad Reza Halvagar
Vahid Amani
Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal
SynOpen
thioazlactone
nitroketene dithioacetal
bicyclic pyridine
dithiocarbamate
catalyst-free
author_facet Marziyeh Saeedi
Maryam Khoshdoun
Salman Taheri
Azim Ziyaei Halimehjani
Aliasghar Mohammadi
Mohammad Reza Halvagar
Vahid Amani
author_sort Marziyeh Saeedi
title Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal
title_short Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal
title_full Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal
title_fullStr Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal
title_full_unstemmed Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal
title_sort synthesis of functionalized bicyclic pyridones containing the dithiocarbamate group using thioazlactones, diamines, and nitroketene dithioacetal
publisher Georg Thieme Verlag KG
series SynOpen
issn 2509-9396
publishDate 2021-04-01
description 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.
topic thioazlactone
nitroketene dithioacetal
bicyclic pyridine
dithiocarbamate
catalyst-free
url http://www.thieme-connect.de/DOI/DOI?10.1055/a-1492-9229
work_keys_str_mv AT marziyehsaeedi synthesisoffunctionalizedbicyclicpyridonescontainingthedithiocarbamategroupusingthioazlactonesdiaminesandnitroketenedithioacetal
AT maryamkhoshdoun synthesisoffunctionalizedbicyclicpyridonescontainingthedithiocarbamategroupusingthioazlactonesdiaminesandnitroketenedithioacetal
AT salmantaheri synthesisoffunctionalizedbicyclicpyridonescontainingthedithiocarbamategroupusingthioazlactonesdiaminesandnitroketenedithioacetal
AT azimziyaeihalimehjani synthesisoffunctionalizedbicyclicpyridonescontainingthedithiocarbamategroupusingthioazlactonesdiaminesandnitroketenedithioacetal
AT aliasgharmohammadi synthesisoffunctionalizedbicyclicpyridonescontainingthedithiocarbamategroupusingthioazlactonesdiaminesandnitroketenedithioacetal
AT mohammadrezahalvagar synthesisoffunctionalizedbicyclicpyridonescontainingthedithiocarbamategroupusingthioazlactonesdiaminesandnitroketenedithioacetal
AT vahidamani synthesisoffunctionalizedbicyclicpyridonescontainingthedithiocarbamategroupusingthioazlactonesdiaminesandnitroketenedithioacetal
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