Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles

[Image: see text] Dimethyl carbonimidodithioates, 2 derived from various primary aryl amines (1) by reacting with carbon disulfide and methyl iodide in dimethyl formamide in the presence of concentrated sodium hydroxide, are converted to the diaziridine derivatives, 3 by reacting with hydrazine in e...

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Autores principales: Moirangthem, Shyamkanhai S., Ahanthem, Dini, Khongbantabam, Sanatombi D., Laitonjam, Warjeet S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9453805/
https://www.ncbi.nlm.nih.gov/pubmed/36092588
http://dx.doi.org/10.1021/acsomega.2c03622
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author Moirangthem, Shyamkanhai S.
Ahanthem, Dini
Khongbantabam, Sanatombi D.
Laitonjam, Warjeet S.
author_facet Moirangthem, Shyamkanhai S.
Ahanthem, Dini
Khongbantabam, Sanatombi D.
Laitonjam, Warjeet S.
author_sort Moirangthem, Shyamkanhai S.
collection PubMed
description [Image: see text] Dimethyl carbonimidodithioates, 2 derived from various primary aryl amines (1) by reacting with carbon disulfide and methyl iodide in dimethyl formamide in the presence of concentrated sodium hydroxide, are converted to the diaziridine derivatives, 3 by reacting with hydrazine in ethanol. The diaziridines, 3 on oxidation with lead tetraacetate in refluxing xylene, extrudes nitrogen, and intramolecular stabilization, particularly 1,2-carbon migration, takes place to give the product, 5. The reaction may take place through the intermediates, diazirines, 4, which have not been isolated. This work provides a new approach for the conversion of aryl amines having no α-methylene to aryl nitriles.
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spelling pubmed-94538052022-09-09 Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles Moirangthem, Shyamkanhai S. Ahanthem, Dini Khongbantabam, Sanatombi D. Laitonjam, Warjeet S. ACS Omega [Image: see text] Dimethyl carbonimidodithioates, 2 derived from various primary aryl amines (1) by reacting with carbon disulfide and methyl iodide in dimethyl formamide in the presence of concentrated sodium hydroxide, are converted to the diaziridine derivatives, 3 by reacting with hydrazine in ethanol. The diaziridines, 3 on oxidation with lead tetraacetate in refluxing xylene, extrudes nitrogen, and intramolecular stabilization, particularly 1,2-carbon migration, takes place to give the product, 5. The reaction may take place through the intermediates, diazirines, 4, which have not been isolated. This work provides a new approach for the conversion of aryl amines having no α-methylene to aryl nitriles. American Chemical Society 2022-08-22 /pmc/articles/PMC9453805/ /pubmed/36092588 http://dx.doi.org/10.1021/acsomega.2c03622 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Moirangthem, Shyamkanhai S.
Ahanthem, Dini
Khongbantabam, Sanatombi D.
Laitonjam, Warjeet S.
Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles
title Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles
title_full Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles
title_fullStr Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles
title_full_unstemmed Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles
title_short Facile Conversion of Aryl Amines Having No α-Methylene to Aryl Nitriles
title_sort facile conversion of aryl amines having no α-methylene to aryl nitriles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9453805/
https://www.ncbi.nlm.nih.gov/pubmed/36092588
http://dx.doi.org/10.1021/acsomega.2c03622
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