SYNTHESIS AND CHARACTERISATION OF 2-AMINOCHALCONES, AND 1,4-BIS(2-AMINOPHENYL)-2-PHENYLBUTANE-1,4-DIONE DERIVATIVES

RIZKY HIDAYATI, Dr. Tutik Dwi Wahyuningsih, M. Si.; Dr. Endang Astuti, M. Si.

2019 | Skripsi | S1 KIMIA

Sintesis turunan 2-aminokalkon dari 2-aminoasetofenon dan beberapa macam aldehida melalui reaksi Claisen-Schmidt telah dilakukan. Reaksi dari turunan 2-aminokalkon tersebut dengan 2-oksindol juga telah dilakukan untuk memperoleh turunan 1,4-bis(2-aminofenil)-2-fenilbutana-1,4-dion melalui proses adisi Michael-oksidasi-pembelahan cincin. Sintesis 2-aminokalkon dilakukan dengan mereaksikan 2-aminoasetofenon dan aldehida yang berbeda, yaitu benzaldehida, 4-klorobenzaldehida, tiofena-2-karbaldehida, dan 4-metoksibenzaldehida dengan adanya natrium hidroksida (NaOH) dalam etanol pada suhu ruangan selama 18 jam untuk menghasilkan berturut-turut senyawa (E)-1-(2-aminophenyl)-3-phenylprop-2-en-1-one (3a), (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one (3b), (E)-1-(2-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one (3c), dan (E)-1-(2-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (3d). 2-Aminokalkon 3a-d selanjutnya direaksikan dengan 2-oksindol dengan adanya NaOH dalam dimetil sulfoksida (DMSO) pada suhu ruangan selama 5-6 jam untuk menghasilkan senyawa 5a-d, yaitu 1,4-bis(2-aminophenyl)-2-phenylbutane-1,4-dione (5a), 1,4-bis(2-aminophenyl)-2-(4-chlorophenyl)butane-1,4-dione (5b), 1,4-bis(2-aminophenyl)-2-(thiophen-2-yl)butana-1,4-dione (5c), dan 1,4-bis(2-aminophenyl)-2-(4-methoxyphenyl)butane-1,4-dione (5d). Semua produk yang disintesis dikarakterisasi dengan menggunakan 1H- dan 13C-NMR, FTIR atau FT-NSI spektrometer. Dari sintesis turunan 2-aminokalkon, kalkon 3a-d telah berhasil disintesis dengan persentase hasil berturut-turut 62,3, 86,2, 72,9, dan 41,6%. Selanjutnya, reaksi Michael adisi terhadap kalkon 3a-d dan 2-oksindol juga telah dilakukan menghasilkan senyawa 1,4-dione 5a-d dengan persentase hasil masing-masing 42,4, 46,2, 57,1, dan 35,3%.

Synthesis of 2-aminochalcone derivatives from 2-aminoacetophenone and a variety of aldehydes through a Claisen-Schmidt reaction had been carried out. Further reaction of the said 2-aminochalcones with 2-oxindole had also been done to obtain 1,4-bis(2-aminophenyl)-2-phenylbutane-1,4-dione derivatives through a Michael-addition-oxidation-ring cleavage process. The synthesis of 2-aminochalcones was done by reacting 2-aminoacetophenone with different aldehydes, namely benzaldehyde, 4-chlorobenzaldehyde, thiophene-2-carbaldehyde, and 4-methoxybenzaldehyde with the presence of sodium hydroxide (NaOH) in ethanol at room temperature for 18 h to produce (E)-1-(2-aminophenyl)-3-phenylprop-2-en-1-one (3a), (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one (3b), (E)-1-(2-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one (3c), and (E)-1-(2-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (3d), respectively. 2-aminochalcones 3a-d were further reacted with 2-oxindole in the presence of NaOH in dimethyl sulfoxide (DMSO) at room temperature for 5-6 h to give compounds 5a-d, namely 1,4-bis(2-aminophenyl)-2-phenylbutane-1,4-dione (5a), 1,4-bis(2-aminophenyl)-2-(4-chlorophenyl)butane-1,4-dione (5b), 1,4-bis(2-aminophenyl)-2-(thiophen-2-yl)butane-1,4-dione (5c), and 1,4-bis(2-aminophenyl)-2-(4-methoxyphenyl)butane-1,4-dione (5d). All of the synthesized products were characterized by using 1H- and 13C-NMR, FTIR or FT-NSI spectrometers. From the synthesis of 2-aminochalcone derivatives, chalcones 3a-d had been successfully synthesized with the percentage yield of 62.3, 86.2, 72.9, and 41.6%, respectively. Furthermore, 1,4-diones 5a-d had also been successfully produced from Michaels addition reaction of chalcones 3a-d and 2-oxindole in percentage yields of 42.4, 46.2, 57.1, and 35.3%, respectively.

Kata Kunci : 1,4-dione, chalcone, Michael-addition, 2-oxindole