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
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ISSN1477-0520
1477-0539
1477-0539
DOI10.1039/d0ob00887g

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Summary: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.
Bibliography:Electronic supplementary information (ESI) available: Details of optimization, experimental procedures, and characterization of unknown compounds. See DOI
10.1039/d0ob00887g
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SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d0ob00887g