KMID : 1059519990430030302
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Journal of the Korean Chemical Society 1999 Volume.43 No. 3 p.302 ~ p.306
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Synthesis of Novel 1,2-Diazepino[3,4-b]quinoxaline and Pyridazino[3,4-b]quinoxaline Derivatives
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Kim Ho-Sik
Jeong Geuk
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Abstract
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Quinoxaline 4-oxide 10À» 2-chloroacrylonitrile°ú ¹ÝÀÀ½ÃÄÑ 1,3-½Ö±Ø¼º °í¸®È ÷°¡¹ÝÀÀÀ¸·Î 2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline·ù 11a, b¸¦ ÇÕ¼ºÇÏ¿´°í, À̵éÀ» 2,3,4,6-tetrahydro-1H-1,2-diazepino-[3,4-b]quinoxaline 12·Î º¯È¯½ÃÄ×´Ù. ±×¸®°í ??Õ¹?11a¸¦ ¾Æ¼¼Æ®»ê/¹° ¿ë¸Å¿¡¼ SeO2¿Í ¹ÝÀÀ½ÃÄѼ °í¸®º¯È¯¿¡ ÀÇÇØ 1,4-dihydro-4-oxopyridazino[3,4-b]quinoxaline 13À» ÇÕ¼ºÇÏ¿´´Ù.
The 1,3-dipolar cycloaddition reaction of the quinoxaline 4-oxide 10 with 2-chloroacrylonitrile gave the 2,3-dihydro-lH-1,2-diazepino[3,4-blquinoxalines lla, b, respectively, which were converted into the 2,3,4,6-tetrahydro-lH-l,2-diazepino[3,4-b]quinoxaline 12. The reaction of compound lla with selenium dioxide in acetic acid/water resulted in ring transformation to give the 1,4-dihydro-4-oxopyridazino[3,4-blquinoxaline 13.
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