Alfa B -doymamış karbonil bileşiğinin kil katalizörü kullanılarak indol alkaloidlerle vermiş olduğu reaksiyonların incelenmesi
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Date
1998
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Niğde Üniversitesi
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Abstract
ÖZET ap-DOYMAMŞ KARBONİL BİLEŞİĞİNİN KİL KATALİZÖRÜ KULLANILARAK İNDOL ALKALOÎDLERLE VERMİŞ OLDUĞU REAKSİYONLARIN İNCELENMESİ SARIÖZ, Özlem Niğde Üniversitesi Fen Bilimleri Enstitüsü Kimya Ana Bilim Dalı Danışman: Yrd. Doç. Dr. Meysun İbrahim Abdullah Ocak 1998. 82. sayfa İndollerin asit katalizli elektrofilik substitüsyon reaksiyonlarında dimerleşme, polimerleşme gibi yan reaksiyonları önlenmesi için asitliğin kontrolü gerekmektedir. Bu çalışmada doğal asidik montmorillonit kili indol ve türevlerinin dimetilasetilen dikarboksilat ile reaksiyonunda katalizör olarak kullanılmıştır. Bu reaksiyonlardan iyi verimde ürün elde edilmiştir. İndol, N-metil indol, 2-metil indol 3-metil indol ve 1,3-dimetil indolün kil katalizörlüğünde dimetilasetilen dikarboksilat ile reaksiyonundan sırası ile 3.3'-diindolil- süksinik-dimetil ester, 3,3-diindolil-l-metil- süksinik-dimetil ester, 2-metil-indolil (3)- maleik-dimetil ester ve 2-metil- 3,4-bis metoksi karbonil- lH-1-benzazepin, 2,2'-diindolil-3- metil-süksinik-dimetil ester, l,5-dimetil-3,4- bis metoksi karbonil- lH-1-benzazepin elde edilmiştir. Bileşiklerin yapıları İR, lR NMR, MS ve elementel analiz teknikleri ile aydınlatılmıştır. Anahtar Sözcükler: İndol. Elektrofilik Substitüsyon. Kil.Montmorillonit. m
SUMMARY SARIÖZ. Özlem Niğde University Graduate School of Natural and Applied SciencesDepartment of Chemistry Supervisor: Dr. Meysun Ibrahim Abdullah December 1998. 82 pages Electrophilic substitution of indoles in the presence of an acid requires careful control of acidity to prevent side reactions such as dimerisation and polymerisation. In this work, the acidic nature of montmorillonite clay has been used to catalyse the reaction of indole and its derivatives with the a,B-unsaturated ester, dimethyl acetylene dicarboxylate. These reactions occured more readily and specifically and gave products in good yields. Thus the reaction of indole and N-methyl indole with dimethyl acetylene dicarboxylate gave 3.3'- diindolyl- succinic-dimethyl ester and 3,3'-diindolyl-l -methyl- succinic-dimethyl ester, respectively, while the reaction with 2-methyl indole produced, 2-methyl-indolyl (3)- rnaleic-dimethyl ester and 2-methyl- 3,4-bis methoxy çarbonyl-lH-1-benzazapine. The reaction with 3-methyl indole yielded 2,2'-diindolyl-3-methyl-succinic-dimethyl ester, whereas the reaction with 1,3-dimethyl indole produced l,5-dimethyl-3,4- bis methoxy carbonyl-lH-1-benzazepine. The structure of these compounds has been identified by *H NMR, IR, MS and elemental analysis techniques. Key Words: Indole. Electrophilic substitution. Clay. Montmorillonite IV
SUMMARY SARIÖZ. Özlem Niğde University Graduate School of Natural and Applied SciencesDepartment of Chemistry Supervisor: Dr. Meysun Ibrahim Abdullah December 1998. 82 pages Electrophilic substitution of indoles in the presence of an acid requires careful control of acidity to prevent side reactions such as dimerisation and polymerisation. In this work, the acidic nature of montmorillonite clay has been used to catalyse the reaction of indole and its derivatives with the a,B-unsaturated ester, dimethyl acetylene dicarboxylate. These reactions occured more readily and specifically and gave products in good yields. Thus the reaction of indole and N-methyl indole with dimethyl acetylene dicarboxylate gave 3.3'- diindolyl- succinic-dimethyl ester and 3,3'-diindolyl-l -methyl- succinic-dimethyl ester, respectively, while the reaction with 2-methyl indole produced, 2-methyl-indolyl (3)- rnaleic-dimethyl ester and 2-methyl- 3,4-bis methoxy çarbonyl-lH-1-benzazapine. The reaction with 3-methyl indole yielded 2,2'-diindolyl-3-methyl-succinic-dimethyl ester, whereas the reaction with 1,3-dimethyl indole produced l,5-dimethyl-3,4- bis methoxy carbonyl-lH-1-benzazepine. The structure of these compounds has been identified by *H NMR, IR, MS and elemental analysis techniques. Key Words: Indole. Electrophilic substitution. Clay. Montmorillonite IV
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Fen Bilimleri Enstitüsü, Kimya Ana Bilim Dalı
Fen Bilimleri Enstitüsü, Kimya Ana Bilim Dalı
Keywords
Kimya, Chemistry
