Tetrahedron ( IF 2.1 ) Pub Date : 2010-08-21 , DOI: 10.1016/j.tet.2010.08.044 Maroš Bella , Marcel Schultz , Viktor Milata , Katarína Koňariková , Martin Breza
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 selenadiazolo[3,4-h]quinolones 9. Acid hydrolysis of etyl ester 9c afforded corresponding acid 10. All prepared selenadiazoloquinolones were tested for antimicrobial activity.
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Gould–Jacobs反应在4-氨基-2,1,3-苯并硒二唑中的应用
已经描述了合成4-氨基-2,1,3-苯并硒基二唑(4)的有效方法。用SnCl 2 ·2H 2 O还原易得的4-硝基苯并噻二唑6,得到1,2,3-三氨基苯二盐酸盐2。后者在用SeO 2水溶液处理后提供所需的胺4。活化烯醇醚7与胺4的亲核乙烯基取代导致(benzoselenadiazol-4-ylamino)亚甲基衍生物8。衍生物8a – c,e,f的热环化在古尔德-雅各布斯反应条件下,得到了角退火的7-(非)取代的硒代二氮杂[3,4- h ]喹诺酮9。乙酸酯9c的酸水解得到相应的酸10。测试所有制备的硒代二唑并喹诺酮类药物的抗菌活性。