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Application of the Gould-Jacobs reaction to 4-amino-2,1,3-benzoselenadiazole |
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| Authors: | Maroš Bella Viktor Milata Katarína Koňariková |
| Institution: | a Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského street 9, 812 37 Bratislava, Slovak Republic b Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského street 9, 812 37 Bratislava, Slovak Republic c Department of Physical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského street 9, 812 37 Bratislava, Slovak Republic |
| Abstract: | An effective method for the synthesis of 4-amino-2,1,3-benzoselenadiazole (4) has been described. Reduction of readily available 4-nitrobenzothiadiazole 6 with SnCl2·2H2O afforded 1,2,3-triaminobenzene dihydrochloride 2. The latter upon treatment with aqueous SeO2 solution provided desired amine 4. Nucleophilic vinylic substitution of activated enol ethers 7 with amine 4 led to (benzoselenadiazol-4-ylamino)methylene derivatives 8. Thermal cyclization of derivatives 8a-c, e, f under Gould-Jacobs reaction conditions gave angularly annelated 7-(non)substituted selenadiazolo3,4-h]quinolones 9. Acid hydrolysis of etyl ester 9c afforded corresponding acid 10. All prepared selenadiazoloquinolones were tested for antimicrobial activity. |
| Keywords: | Fused selenaheterocycles 2 1 3-Benzoselenadiazoles Quinolones Nucleophilic vinylic substitution Gould-Jacobs reaction |
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