İndol ve türevlerinin michael tipi katılma reaksiyonları
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Date
2007
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Niğde Üniversitesi
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info:eu-repo/semantics/openAccess
Abstract
Bu çalısmada indol, 1-metil- ve 1,3-dimetilindol'ün K-10 Montmorillonit katalizörü varlıgında alfa,beta-doymamıs karbonil bilesiklerinden metil propiolat ve 2-siklopentenonun Michael tipi katılma tepkimeleri incelenmistir. Bu reaksiyonlardan iyi verimle katılma, bis-, tris-indolil ve halkalasma ürünleri elde edilmistir. ndol ile metilpropiolatın reaksiyonundan bir diindolil bilesigi, metil 3,3-di(1H-indol-3-il) propanoat elde edilmistir. 1-metilindolün metilpropiolat ile reaksiyonundan ise metil 3,3-bis(1-metil- 1H-indol-3-il) propanoat bilesigi sentezlenmistir. Aynı reaktif ile 1,3-dimetilindolün reaksiyonundan sırasıyla; metil 3,3-bis(1,3-dimetil-1H-indol-2-il) propanoat, metil 3,3,3-tris(1,3-dimetil-1H-indol-2-il) propanoat ve metil 1,5-dimetil-1H-benzo[b]azopin- 3-karboksilat halkalasma ürünü elde edilmistir. Ayrıca indol, 1-metil- ve 1,3- dimetilindolün 2-siklopentenon ile reaksiyonları sonucunda sırasıyla; 3-(1H-indol-3-il) siklopentanon bilesigi, 3-(1-metil-1H-indol-3-il) siklopentanon ve 3-(1,2-dimetil-1Hindol- 3-il) siklopentanon katılma ürünleri sentezlenmistir. Anahtar Sözcükler: İndol, Michael Katılma, Kil, Montmorillonit, 2-Siklopentenon, Metilpropiolat
In this work, Micheal type reactions of indole, 1-methyl- and 1,3-dimethylindole with the alfa,beta unsaturated carbonyl methyl propiolate and 2-cyclopentenone in the presence of K-10 Montmorillonit was investigated. These reactions gave addition, cyclization as well as bis- and tris- indolyl products in a good yield. The reaction of indole with methyl propiolate produced the diindolyl methyl 3,3-di(1H-indol-3-yl) propanoate compound while the reaction of N-methyl indole with methyl propiolate gave methyl 3,3-bis(1-methyl-1H-indol-3-yl) propanoate. However, the reaction of 1,3- dimethylindole withe the same reactant yielded methyl 3,3-bis(1,3-dimethyl-1H-indol- 2-yl) propanoate, methyl 3,3,3-tris(1,3-dimethyl-1H-indol-2-yl) propanoate and the cyclic product methyl 1,5-dimethyl-1H-benzo[b]azopine-3-carboxylate repectively. Meanwhile the reaction of indole, 1-methyl- and 1,3-dimethylindole with 2- cyclopentenone gave 3-(1H-indol-3-yl) cyclopentanone, 3-(1-methyl-1H-indol-3-yl) cyclopentanon and the 3-(1,2-dimethyl-1H-indol-3-yl) cyclopentanone addition products respectively. Keywords: ndole, Michael Addition, Clay, Montmorillonite, 2-Cyclopentenone, Methylpropiolate.
In this work, Micheal type reactions of indole, 1-methyl- and 1,3-dimethylindole with the alfa,beta unsaturated carbonyl methyl propiolate and 2-cyclopentenone in the presence of K-10 Montmorillonit was investigated. These reactions gave addition, cyclization as well as bis- and tris- indolyl products in a good yield. The reaction of indole with methyl propiolate produced the diindolyl methyl 3,3-di(1H-indol-3-yl) propanoate compound while the reaction of N-methyl indole with methyl propiolate gave methyl 3,3-bis(1-methyl-1H-indol-3-yl) propanoate. However, the reaction of 1,3- dimethylindole withe the same reactant yielded methyl 3,3-bis(1,3-dimethyl-1H-indol- 2-yl) propanoate, methyl 3,3,3-tris(1,3-dimethyl-1H-indol-2-yl) propanoate and the cyclic product methyl 1,5-dimethyl-1H-benzo[b]azopine-3-carboxylate repectively. Meanwhile the reaction of indole, 1-methyl- and 1,3-dimethylindole with 2- cyclopentenone gave 3-(1H-indol-3-yl) cyclopentanone, 3-(1-methyl-1H-indol-3-yl) cyclopentanon and the 3-(1,2-dimethyl-1H-indol-3-yl) cyclopentanone addition products respectively. Keywords: ndole, Michael Addition, Clay, Montmorillonite, 2-Cyclopentenone, Methylpropiolate.
Description
Fen Bilimleri Enstitüsü, Kimya Ana Bilim Dalı
Keywords
Kimya, Chemistry
