YENİ PİRROL-2,3-DİON’LARIN BAZI ALKOL, AMİN VE DİAMİNLERLE REAKSİYONLARININ İNCELENMESİ

Year 2002, Volume: 18 Issue: 1, 92 - 98, 01.06.2002

İsmail Yıldırım Yunus Akçamur

Abstract

N,N-dimetilüre ve N,N-dietilüre ile 4-benzoil-5-fenil-2,3-furandion’un reaksiyonundan bir molekül H2O ayrılması sonucunda, sırasıyla 4-benzoil-1-(N,N-dimetilkarbamoil)-5-fenil-2,3-pirroldion (1a) ve 4-benzoil-1-(N,N-dietilkarbamoil)-5fenil-2,3-pirroldion (1b) oluşur. Bu çalışmada, alkoller, arilaminler ve arildiaminler gibi çeşitli nükleofillerle 1a,b bileşiklerinin farklı şartlardaki reaksiyonları incelendi. Böylece, yeni alkil-3-benzoil-4-(3,3-dialkilüreido)-2-okso-4-fenil-3-butenoat türevleri olan esterler (2a,b,c), 2-pirrolon türevleri (3a,b,c) ve bazı tetrahidrokinoksalin-2-on türevi (4a,b) bileşikler sentez edildi. Bu bileşiklerin yapıları, elementel analiz, IR, 1H-NMR ve 13C-NMR spektroskopisi yardımıyla aydınlatıldı

Keywords

Pirrol-2, 3-dion, N, N-dietilüre, Arilamin, Nükleofilik katılma reaksiyonu

THE INVESTIGATIONS OF THE REACTIONS OF SOME ALCOHOLS, AMINES AND DIAMINES WITH NEW PYRROL-2,3-DIONES

Abstract

N,N-dimethylurea and N,N-diethylurea react with 4-benzoyl-5-phenyl-2,3-furandione by the elimination of H2O molecule to give 4-benzoyl-1-(N,N-dimethylcarbamoyl)-5-phenyl-2,3-pyrroldione (1a) and 4-benzoyl-1-(N,Ndiethylcarbamoyl)-5-phenyl-2,3-pyrroldione (1b), respectively. In this study, the investigations were extended to the reactions of 1a,b with various nucleophiles such as alcohols, arylamines and aryldiamines at different conditions. Thus, new various alkyl-3benzoyl-4-(3,3-dialkyl ureido)-2-oxo-4-phenyl-3-butenoate derivatives (2a,b,c), 2-pyrrolone derivatives (3a,b,c) and some tetrahydro quinoxalin-2-one derivatives (4a,b) were synthesized. The structures of these compounds were determined by the 13C-, 1H-NMR, IR spectroscopic data and elemental analyses

Keywords

Pyrrol-2, 3-dione, N, N-diethylurea, Arylamine, Nucleophilic addition reaction