Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous Medium

Benzazole-2-ones (benzimidazolones, benzothiazolones, benzoxazolones) are important derivatives of benzazole compounds that exist widely in many biologically and pharmaceutically active molecules. Furthermore, benzazole-2-one derivatives also have many applications in agrochemical and material scien...

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Main Authors: Esmail Vessally, Somayeh Mohammadi, Morteza Abdoli, Akram Hosseinian, Parisa Ojaghloo
Format: Article
Language:English
Published: Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR 2020-10-01
Series:Iranian Journal of Chemistry & Chemical Engineering
Subjects:
Online Access:http://www.ijcce.ac.ir/article_36288_52716342806f57045441185ecf1aa7c2.pdf
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author Esmail Vessally
Somayeh Mohammadi
Morteza Abdoli
Akram Hosseinian
Parisa Ojaghloo
author_facet Esmail Vessally
Somayeh Mohammadi
Morteza Abdoli
Akram Hosseinian
Parisa Ojaghloo
author_sort Esmail Vessally
collection DOAJ
description Benzazole-2-ones (benzimidazolones, benzothiazolones, benzoxazolones) are important derivatives of benzazole compounds that exist widely in many biologically and pharmaceutically active molecules. Furthermore, benzazole-2-one derivatives also have many applications in agrochemical and material science. Herein, a novel, practical and green synthesis of titled compounds by the reaction of aniline derivatives with inexpensive and easily accessible sodium cyanate has been reported. Good to excellent yields of products have been obtained under catalyst- and ligand-free conditions in water as solvent. This procedure avoids the use of time-consuming and tedious column chromatography and the products were easily isolated by simple extraction followed by washing with dichloromethane.
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spelling doaj.art-e9e443e428c9489aa8cdd72dc89920922022-12-21T20:12:18ZengIranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECRIranian Journal of Chemistry & Chemical Engineering1021-99861021-99862020-10-01395111910.30492/ijcce.2019.3628836288Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous MediumEsmail Vessally0Somayeh Mohammadi1Morteza Abdoli2Akram Hosseinian3Parisa Ojaghloo4Department of Chemistry, Payame Noor University, Tehran, I.R. IRANDepartment of Chemistry, Payame Noor University, Tehran, I.R. IRANDepartment of Chemistry, Payame Noor University, Tehran, I.R. IRANSchool of Engineering Science, College of Engineering, University of Tehran, Tehran, I.R. IRANDepartment of Chemistry, Payame Noor University, Tehran, I.R. IRANBenzazole-2-ones (benzimidazolones, benzothiazolones, benzoxazolones) are important derivatives of benzazole compounds that exist widely in many biologically and pharmaceutically active molecules. Furthermore, benzazole-2-one derivatives also have many applications in agrochemical and material science. Herein, a novel, practical and green synthesis of titled compounds by the reaction of aniline derivatives with inexpensive and easily accessible sodium cyanate has been reported. Good to excellent yields of products have been obtained under catalyst- and ligand-free conditions in water as solvent. This procedure avoids the use of time-consuming and tedious column chromatography and the products were easily isolated by simple extraction followed by washing with dichloromethane.http://www.ijcce.ac.ir/article_36288_52716342806f57045441185ecf1aa7c2.pdfbenzazole-2-onesbenzimidazolones, benzothiazolonesbenzoxazolonessodium cyanategreen chemistrywatersynthesis
spellingShingle Esmail Vessally
Somayeh Mohammadi
Morteza Abdoli
Akram Hosseinian
Parisa Ojaghloo
Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous Medium
Iranian Journal of Chemistry & Chemical Engineering
benzazole-2-ones
benzimidazolones, benzothiazolones
benzoxazolones
sodium cyanate
green chemistry
water
synthesis
title Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous Medium
title_full Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous Medium
title_fullStr Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous Medium
title_full_unstemmed Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous Medium
title_short Convenient and Robust Metal-Free Synthesis of Benzazole-2-Ones Through the Reaction of Aniline Derivatives and Sodium Cyanate in Aqueous Medium
title_sort convenient and robust metal free synthesis of benzazole 2 ones through the reaction of aniline derivatives and sodium cyanate in aqueous medium
topic benzazole-2-ones
benzimidazolones, benzothiazolones
benzoxazolones
sodium cyanate
green chemistry
water
synthesis
url http://www.ijcce.ac.ir/article_36288_52716342806f57045441185ecf1aa7c2.pdf
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