DDQ in mechanochemical C–N coupling reactions

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) condi...

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Autores principales: Bera, Shyamal Kanti, Bhanja, Rosalin, Mal, Prasenjit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9174842/
https://www.ncbi.nlm.nih.gov/pubmed/35706992
http://dx.doi.org/10.3762/bjoc.18.64
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author Bera, Shyamal Kanti
Bhanja, Rosalin
Mal, Prasenjit
author_facet Bera, Shyamal Kanti
Bhanja, Rosalin
Mal, Prasenjit
author_sort Bera, Shyamal Kanti
collection PubMed
description 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) conditions. In the presence of DDQ, the intramolecular C(sp(2))–H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes resulted in substituted quinazolin-4(3H)-one derivatives in high yields.
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spelling pubmed-91748422022-06-14 DDQ in mechanochemical C–N coupling reactions Bera, Shyamal Kanti Bhanja, Rosalin Mal, Prasenjit Beilstein J Org Chem Full Research Paper 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) conditions. In the presence of DDQ, the intramolecular C(sp(2))–H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes resulted in substituted quinazolin-4(3H)-one derivatives in high yields. Beilstein-Institut 2022-06-01 /pmc/articles/PMC9174842/ /pubmed/35706992 http://dx.doi.org/10.3762/bjoc.18.64 Text en Copyright © 2022, Bera et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Bera, Shyamal Kanti
Bhanja, Rosalin
Mal, Prasenjit
DDQ in mechanochemical C–N coupling reactions
title DDQ in mechanochemical C–N coupling reactions
title_full DDQ in mechanochemical C–N coupling reactions
title_fullStr DDQ in mechanochemical C–N coupling reactions
title_full_unstemmed DDQ in mechanochemical C–N coupling reactions
title_short DDQ in mechanochemical C–N coupling reactions
title_sort ddq in mechanochemical c–n coupling reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9174842/
https://www.ncbi.nlm.nih.gov/pubmed/35706992
http://dx.doi.org/10.3762/bjoc.18.64
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AT bhanjarosalin ddqinmechanochemicalcncouplingreactions
AT malprasenjit ddqinmechanochemicalcncouplingreactions

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