Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

[Image: see text] A straightforward green synthesis of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 6 is reported from ninhydrin 1 via condensation with ethyl acetoacetate, followed by cyclization with hydrazine hydrate in water as a benign solvent. Tetraazafluoranthen-3-thione 7 was obtained usin...

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Autores principales: Boraei, Ahmed T. A., Ghabbour, Hazem A., Sarhan, Ahmed A. M., Barakat, Assem
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7081446/
https://www.ncbi.nlm.nih.gov/pubmed/32201835
http://dx.doi.org/10.1021/acsomega.0c00045
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author Boraei, Ahmed T. A.
Ghabbour, Hazem A.
Sarhan, Ahmed A. M.
Barakat, Assem
author_facet Boraei, Ahmed T. A.
Ghabbour, Hazem A.
Sarhan, Ahmed A. M.
Barakat, Assem
author_sort Boraei, Ahmed T. A.
collection PubMed
description [Image: see text] A straightforward green synthesis of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 6 is reported from ninhydrin 1 via condensation with ethyl acetoacetate, followed by cyclization with hydrazine hydrate in water as a benign solvent. Tetraazafluoranthen-3-thione 7 was obtained using Lawesson’s reagent. N-alkylated tetraazafluoranthen-3-one 8–12 and S-alkylated analogues 13–15 were synthesized via alkylation. The investigation of the unique reactivity of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one/thione toward the alkylation and aza-Michael additions was explored.
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spelling pubmed-70814462020-03-20 Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition Boraei, Ahmed T. A. Ghabbour, Hazem A. Sarhan, Ahmed A. M. Barakat, Assem ACS Omega [Image: see text] A straightforward green synthesis of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 6 is reported from ninhydrin 1 via condensation with ethyl acetoacetate, followed by cyclization with hydrazine hydrate in water as a benign solvent. Tetraazafluoranthen-3-thione 7 was obtained using Lawesson’s reagent. N-alkylated tetraazafluoranthen-3-one 8–12 and S-alkylated analogues 13–15 were synthesized via alkylation. The investigation of the unique reactivity of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one/thione toward the alkylation and aza-Michael additions was explored. American Chemical Society 2020-03-03 /pmc/articles/PMC7081446/ /pubmed/32201835 http://dx.doi.org/10.1021/acsomega.0c00045 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Boraei, Ahmed T. A.
Ghabbour, Hazem A.
Sarhan, Ahmed A. M.
Barakat, Assem
Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition
title Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition
title_full Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition
title_fullStr Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition
title_full_unstemmed Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition
title_short Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition
title_sort expeditious green synthesis of novel 4-methyl-1,2,5,6-tetraazafluoranthen-3(2h)-one analogue from ninhydrin: n/s-alkylation and aza-michael addition
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7081446/
https://www.ncbi.nlm.nih.gov/pubmed/32201835
http://dx.doi.org/10.1021/acsomega.0c00045
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