Sulfur-mediated annulation of 1,2-phenylenediamines towards benzofuro- and benzothieno-quinoxalines

We report a method for condensation between ortho -phenylenediamines and ortho -hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 29; pp. 5652 - 5659
Main Authors Tran, Loan T, Ho, Tuan H, Phan, Nhu T. A, Nguyen, Tung T, Phan, Nam T. S
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.08.2020
Royal Society of Chemistry
Subjects
Chemical reactions
Chemistry
Chemistry, Organic
Optimization
Physical Sciences
Quinoxalines
Science & Technology
Sulfur
ELEMENTAL SULFUR
OXIMES
HETEROCYCLES
ACCESS
Online AccessGet full text
ISSN1477-0520
1477-0539
1477-0539
DOI10.1039/d0ob00887g

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Abstract We report a method for condensation between ortho -phenylenediamines and ortho -hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines from ortho -chloroacetophenones. Oxidation of sp 3 C-H bonds in acetophenones is exploited to annulate with 1,2-phenylenediamines.
AbstractList We report a method for condensation between ortho-phenylenediamines and ortho-hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines from ortho-chloroacetophenones.We report a method for condensation between ortho-phenylenediamines and ortho-hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines from ortho-chloroacetophenones.
We report a method for condensation between ortho -phenylenediamines and ortho -hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines from ortho -chloroacetophenones. Oxidation of sp 3 C-H bonds in acetophenones is exploited to annulate with 1,2-phenylenediamines.
We report a method for condensation between ortho-phenylenediamines and ortho-hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines from ortho-chloroacetophenones.
We report a method for condensation between ortho -phenylenediamines and ortho -hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines from ortho -chloroacetophenones.
We report a method for condensation betweenortho-phenylenediamines andortho-hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines fromortho-chloroacetophenones.
Author Tran, Loan T
Phan, Nam T. S
Nguyen, Tung T
Ho, Tuan H
Phan, Nhu T. A
AuthorAffiliation Faculty of Chemical Engineering
Vietnam National University Ho Chi Minh City
Ho Chi Minh City University of Technology (HCMUT)
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Keywords ELEMENTAL SULFUR
OXIMES
HETEROCYCLES
ACCESS
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Snippet We report a method for condensation between ortho -phenylenediamines and ortho -hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded...
We report a method for condensation betweenortho-phenylenediamines andortho-hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in...
We report a method for condensation between ortho-phenylenediamines and ortho-hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in...
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SubjectTerms Chemical reactions
Chemistry
Chemistry, Organic
Optimization
Physical Sciences
Quinoxalines
Science & Technology
Sulfur
Title Sulfur-mediated annulation of 1,2-phenylenediamines towards benzofuro- and benzothieno-quinoxalines
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