3-Oksopropannitrillerin seryum(IV) amonyum nitrat ve mangan(III) asetat aracılığıyla konjuge dienlerle radikal halkalaşma reaksiyonları

Abstract

Bu çalışma, 3-oksopropannitrillerin radikal yükseltgen seryum(IV) amonyum nitrat (CAN) ve mangan (III) asetat (MAH) aracılığıyla konjuge dienlerle radikal halkalaşma reaksiyonlarını içermektedir. Araştırmada 3-oksopropannitril bileşiği olarak 3-fenil-3-oksopropannitril (1a), 3-(4-metilfenil)-3-oksopropannitril (1b), 3-(4-metoksifenil)-3-oksopropannitril (1c), 3-(4-klorfenil)-3-oksopropannitril (1d), 3-(2-tiyenil)-3-oksopropannitril (1e), 3-(2-furil)-3-oksopropannitril (1f), 3-(2-benzofuranil)-3-oksopropannitril (1g), 3-ter-butil-3-oksopropannitril (1h) kullanıldı. Konjuge dien olarak (1E)-büta-1,3-dien-1-ilbenzen (2a), 2-[(1E)-büta-1,3-dien-1-il]tiyofen (2b), 1,1'-büta-1,3-dien-1,1'-diildibenzen (2c), [(1E)-3-metilbüta-1,3-dien-1-il]benzen (2d), 2-[(1E)-3-metilbüta-1,3-dien-1-il]tiyofen (2e), [(1E)-3-fenilbüta-1,3-dien-1-il]benzen (2f) kullanıldı. Radikal yükseltgen olarak CAN ve MAH kullanıldı. 3-Oksopropannitrillerin CAN ve MAH aracılığıyla konjuge dienlerle reaksiyonları sonucunda 5-vinil sübstitüe 3-siyano-4,5-dihidrofuranlar (3a-h, 4a-b, 5a-d, 6a-g, 7a-c, 8a-e) elde edildi. Elde edilen ürünler kolon ve preperatif ince tabaka kromotografisi kullanılarak saflaştırıldı. Bileşiklerin yapıları spektroskopik yöntemler (IR, 1H-NMR, 13C-NMR ve kütle spektrumu) ile aydınlatıldı.

This study covers the radical cyclizations of 3-oxopropanenitriles with conjugated dienes mediated by radical oxidants cerium(IV) ammonium nitrate (CAN) and manganese(III) acetate. In the study, 3-phenyl-3-oxopropanenitrile (1a), 3-(4-methylphenyl)-3- oxopropanenitrile (1b), 3-(4-methoxyphenyl)-3-oxopropanenitrile (1c), 3-(4-cholorophenyl)-3-oxopropanenitrile (1d), 3-(2-thienyl)-3-oxopropanenitrile (1e), 3-(2-furyl)-3-oxopropanenitrile (1f), 3-(2-benzofuranyl)-3-oxopropanenitrile (1g), 3-ter-butyl-3- oxopropanenitrile (1h) were used as 3-oxopropanenitriles. (1E)-Buta-1,3-diene-1-ylbenzene (2a), 2-[(1E)-buta-1,3-diene-1-yl]thiophene (2b), 1,1?-buta-1,3-diene-1,1?-diyldibenzene (2c), [(1E)-3-methylbuta-1,3-diene-1-yl]benzene (2d), 2-[(1E)-3-methylbuta-1,3-diene-1-yl]thiophene (2e), [(1E)-3-phenylbuta-1,3-diene-1-yl]benzene (2f) were used as conjugated dienes. CAN and MAH were used as radical oxidants.CAN and MAH mediated reactions of 3-oxopropanenitriles with conjugated dienes led to the formation of 5-vinyl substituted 3-cyano-4,5-dihydrofurans (3a-h, 4a-b, 5a-d, 6a-g, 7a-c, 8a-e). Products obtained were purified through coloumn and preparative thin layer chromatography. Structures of compounds were characterized by spectroscopic methods (IR, 1H-NMR, 13C-NMR and mass).