1苯甲酰基3芳基咪浴类衍生物的合成.pdfVIP

摘 要 本文研究了 1一苯甲酞基一3一芳基硫脉 (la-f)与丙酮/滨、苯乙酮/澳在三乙 胺存在下的成环反应。结果表明在三乙胺过量时，化合物la--f与丙酮/漠生成1- 苯甲酞基一3一芳基一4-轻基一4一甲基咪哇琳-2一硫酮 (3a-f);而当三乙胺与原料 la-f 等摩尔时则生成 1一苯甲酞基一3一芳基一4一甲基咪哇-2一硫酮 (4a-f)。将化合物 3a-f 溶于适当的溶剂中然后加热或加入酸，则化合物3a-f顺利地转化成4a-f。类似 地，1一苯甲酞基一3一芳基硫腺 (la-f)与苯乙酮/澳在三乙胺过量或等摩尔反应时 分别生成 1一苯甲酸基一3一芳基一4-轻基一4一苯基咪哇琳-2-硫酮 (5a-f)和 1一苯甲酸 基一3一芳基一苯基咪哇-2-硫酮 (6a-f)。所有产物的结构均经元素分析、红外、 质谱和核磁共振光谱所证实。此外，还尝试了1一苯甲酞基一3一芳基硫脉 (la--f) 与丁酮/澳、乙醛/澳在三乙胺存在下的反应。 关键词:1-苯甲酞基一3一芳基硫服，咪哇琳-2一硫酮衍生物， 咪哇-2一硫酮衍 生物。 ABSTRACT Thereactionof1-benzoyl-3-arylthioureas(la-f)withacetonetbromineand acetophenone/bromineinthepresenceoftriethylaminewasdescribed.Theresults showedthatthestructure.ofproductsdependedonthetriethylamine.Inthecaseof excesstriethylamineispresent,thereactionof1-benzoyl-3-arylthioureas(la-f)with acetone/brominegavethe 1-benzoyl-3-aryl-4-hydroxy-4-methylimidazoline-2- thiones(3a刃 Ontheotherhand,iftheratioofcompoundsla-fandtriethylamineis equal, the product is 1-benzoyl-3-aryl-4-methylimidazole-2-thiones (4a--f). Interestingly,compounds3a-fcanbetransformedto4a-fwhenthesolutionof3a-f washeatedoradditionofacid.Therefore,wecanconcludethatthereactionof1- benzoyl-3-arylthioureas(la-f)withacetone/bromineaffordedthe1-benzoyl-3-aryl-4- hydroxy-4-methylimidazoline-2-thiones(3a--f)firstly,iftriethylamineisexcess compounds3a-fare stableandthencanbeisolated ifnotso,compounds3a-f transformedto4a-fautomaticallyundertheconditionofreaction.Similarly,the reactionof1-benzoyl-3-arylthioureas(1a-f)withacetophenone/brominewascarried outinthepresenceofexcessorequalmolartriethylamine,1-benzoyl-3-aryl-4- hydroxy-4-phenylimidazoline-2-thiones(5a-f)and1-benzoyl-3-aryl-4-phenylimida- zole-2-thiones(6a-f)wereobtained,respectively.Thestructuresof3a-f,4a-f,Sa-f and6a-fwereconfirmedbyIR,IVMR,MSspectranadelementalanalyses.Inaddition, thereactionof1-benzoyl-3-arylthioureas(la-0withbutanone/bromineand acetaldehyde/bromineinthepre