Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives

[Image: see text] Herein, we report a new approach to synthesize a series of 1,2,4-[e]-benzotriazine and cinnoline derivatives from 3-substituted isoindolin-1-one. All the reported products are obtained through an economical two-step synthetic procedure resulting in fair-to-high yields. Cinnolines (...

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Autores principales: El Dhaibi, Fatat B., Youssef, Ali, Fettinger, James C., Kurth, Mark J., Haddadin, Makhluf J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9352262/
https://www.ncbi.nlm.nih.gov/pubmed/35936437
http://dx.doi.org/10.1021/acsomega.2c03045
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author El Dhaibi, Fatat B.
Youssef, Ali
Fettinger, James C.
Kurth, Mark J.
Haddadin, Makhluf J.
author_facet El Dhaibi, Fatat B.
Youssef, Ali
Fettinger, James C.
Kurth, Mark J.
Haddadin, Makhluf J.
author_sort El Dhaibi, Fatat B.
collection PubMed
description [Image: see text] Herein, we report a new approach to synthesize a series of 1,2,4-[e]-benzotriazine and cinnoline derivatives from 3-substituted isoindolin-1-one. All the reported products are obtained through an economical two-step synthetic procedure resulting in fair-to-high yields. Cinnolines (a) and 1,2,4-[e]-benzotriazines (b) result from an intramolecular cyclization of the corresponding 3-substituted isoindolin-1-ones, which, in turn, are prepared by an addition reaction from 2-cyanobenzaldehyde and 2-(2-nitrophenyl) acetonitrile (a) or 2-nitroaniline derivatives (b). A proposed mechanism for this transformation is presented.
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spelling pubmed-93522622022-08-05 Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives El Dhaibi, Fatat B. Youssef, Ali Fettinger, James C. Kurth, Mark J. Haddadin, Makhluf J. ACS Omega [Image: see text] Herein, we report a new approach to synthesize a series of 1,2,4-[e]-benzotriazine and cinnoline derivatives from 3-substituted isoindolin-1-one. All the reported products are obtained through an economical two-step synthetic procedure resulting in fair-to-high yields. Cinnolines (a) and 1,2,4-[e]-benzotriazines (b) result from an intramolecular cyclization of the corresponding 3-substituted isoindolin-1-ones, which, in turn, are prepared by an addition reaction from 2-cyanobenzaldehyde and 2-(2-nitrophenyl) acetonitrile (a) or 2-nitroaniline derivatives (b). A proposed mechanism for this transformation is presented. American Chemical Society 2022-07-20 /pmc/articles/PMC9352262/ /pubmed/35936437 http://dx.doi.org/10.1021/acsomega.2c03045 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle El Dhaibi, Fatat B.
Youssef, Ali
Fettinger, James C.
Kurth, Mark J.
Haddadin, Makhluf J.
Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives
title Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives
title_full Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives
title_fullStr Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives
title_full_unstemmed Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives
title_short Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives
title_sort preparation of 3-substituted isoindolin-1-one, cinnoline, and 1,2,4-[e]-benzotriazine derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9352262/
https://www.ncbi.nlm.nih.gov/pubmed/35936437
http://dx.doi.org/10.1021/acsomega.2c03045
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