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Synlett 2020; 31(05): 482-486
DOI: 10.1055/s-0039-1690246
DOI: 10.1055/s-0039-1690246
letter
The Reaction of 6-(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methylcyclohexa-2,4-dien-1-one with Benzene-1,2-diamine: Synthesis and Chemistry of N-(2-Aminophenyl)-2-hydroxy-5-methylbenzimidoyl Cyanide
Further Information
Publication History
Received: 14 October 2019
Accepted after revision: 21 October 2019
Publication Date:
05 November 2019 (online)
![](https://www.thieme-connect.de/media/synlett/202005/lookinside/thumbnails/st-2019-d0545-l_10-1055_s-0039-1690246-1.jpg)
Abstract
(Z)-6-(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methylcyclohexa-2,4-dien-1-one, readily prepared from 4,5-dichloro-1,3,4-dithiazolium chloride and p-cresol, reacts with benzene-1,2-diamine to give N-(2-aminophenyl)-2-hydroxy-5-methylbenzimidoyl cyanide. The latter, in acidic media, cyclizes to give, depending on the reaction conditions, 2-methylbenzofuro[2,3-b]quinoxaline, 2-(1H-benzo[d]imidazol-2-yl)-4-methylphenol or 2-(3-aminoquinoxalin-2-yl)-4-methylphenol.
Key words
1,2,3-dithiazole - imidazole - quinoxaline - benzofuran - ionizing power - carboxylic acid - heterocycle - cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690246.
- Supporting Information
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References and Notes
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For examples of reported biological activities of structurally similar compounds, see: