一种作为抗菌剂的二苯并[c,f]色烯、二苯并[c,h]色烯和苯并[7,8]色烯并[3,4-f]异吲哚的新型合成方法。
A novel synthesis of dibenzo[c,f]chromenes, dibenzo[c,h]chromenes and benzo[7,8]chromeno[3,4-f]isoindoles as antimicrobial agents.
作者信息
el-Gaby M S, Zahran M A, Ismail M M, Ammar Y A
机构信息
Chemistry Department, Faculty of Science, Al-Azhar University at Assiut, Egypt.
出版信息
Farmaco. 2000 Mar;55(3):227-32. doi: 10.1016/s0014-827x(00)00008-2.
Naphtho[2,1-b]pyranone (3) was allowed to react with arylmethylenemalononitriles to yield 4-amino-5-oxo-2-aryl-5H-dibenzo[c,f]chromene-3-carbonitriles (4a,b); with ethyl 3,4-dichlorobenzylidene cyanoacetate to furnish dibenzo[c,f]chromene (5) and with elemental sulfur in dioxane containing piperidine to give thieno[3,4-d]naphtho[2,1-b]pyranone (6). Similarly, naphtho[1,2-b]pyranone (7) was reacted with arylmethylenemalononitriles and elemental sulfur to furnish dibenzo[c,h]chromenes (8) and thieno[3,4-d]naphtho[1,2-b]pyranone (10), respectively. Compound 10 underwent cycloaddition with N-arylmaleimides to yield benzo[7,8]chromeno[3,4-f]isoindoles (11a-c). Some of these compounds were screened in vitro for their antimicrobial activities.
萘并[2,1 - b]吡喃酮（3）与芳基亚甲基丙二腈反应生成4 - 氨基 - 5 - 氧代 - 2 - 芳基 - 5H - 二苯并[c,f]色烯 - 3 - 腈（4a,b）；与3,4 - 二氯亚苄基氰基乙酸乙酯反应得到二苯并[c,f]色烯（5），并与在含哌啶的二氧六环中的元素硫反应生成噻吩并[3,4 - d]萘并[2,1 - b]吡喃酮（6）。类似地，萘并[1,2 - b]吡喃酮（7）分别与芳基亚甲基丙二腈和元素硫反应得到二苯并[c,h]色烯（8）和噻吩并[3,4 - d]萘并[1,2 - b]吡喃酮（10）。化合物10与N - 芳基马来酰亚胺发生环加成反应生成苯并[7,8]色烯并[3,4 - f]异吲哚（11a - c）。对其中一些化合物进行了体外抗菌活性筛选。
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