Abstract

Ullmann reaction of 2-[(6-chloroquinoxalin-2-yl)oxy]benzonitrile with 4-tert-butylphenol unexpect­edly afforded 2-(4-tert-butylphenoxy)-6-chloroquinoxaline instead of the corresponding 6-substituted deriva­tive. Different phenols were used to check the nucleofugality of 2-cyanophenoxy group in the 2-position of quinoxalines, so that 2-cyanophenoxy group can be regarded as an alternative to halogens for nucleophilic substitution. A series of new substituted 6-chloro-2-phenoxyquinoxaline derivatives were synthesized from 4-[(6-chloroquinoxalin-2-yl)oxy]phenol and different heteroaryl and sulfonyl chlorides. The synthesized com­pounds were characterized by IR, ¹H and ¹³C NMR and mass spectra and evaluated for their antibacterial activity.

中文翻译：

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6-氯-2-（2-氰基苯氧基）喹喔啉的亲核取代和苯氧基氯喹喔啉衍生物的抗菌活性

摘要

2-[（（6-氯喹喔啉-2-基）氧基]苄腈与4-叔丁基苯酚的乌尔曼反应出乎意料地提供了2-（4-叔丁基苯氧基）-6-氯喹喔啉而不是相应的6-取代衍生物。使用不同的酚来检查喹喔啉2位上的2-氰基苯氧基的亲核力，因此2-氰基苯氧基可被视为亲核取代的卤素替代品。由4-[（（6-氯喹喔啉-2-基）氧基]苯酚和不同的杂芳基和磺酰氯合成了一系列新的取代的6-氯-2-苯氧基喹喔啉衍生物。所合成的化合物的特征在于IR，¹ H和¹³1 H NMR和质谱，并评价其抗菌活性。