Publication: Etil a- halo-3,4- disübstitüesinnamat ile a- açilamino-3,4- disübstitüesinnamik asit bileşiklerinin sentezi ve pd/ C ile indirgenme ürünleri
Abstract
Bu çalışmada, klasik organik sentez yöntemleri kullanılarak, üçü orjinal altı substrat hazırlandı. Sinnamik asit türevi olan bu substratlar öncül levo dopa bileşikleridir. Prokiral olan bu bileşiklerden; Etil a-bromo-3,4-dimetoksisinnamat (Bileşik 2) ; Etil a-kloro-3,4-dimetoksisinnamat (Bileşik 3) ve Etil a-bromo-3,4-dihidroksisinnamat (Bileşik 4) bileşikleri Wittig Reaksiyonu yöntemiyle ilk kez bu çalışmada sentezlenmiş olup, diğer üç substrat; a-Asetilamino-3-(3,4-dimetoksifenil)sinnamik asit (Bileşik5); a - Asetilamino - 3 - ( 3 , 4 - di - O-asetilfenil)sinnamik asit (Bileşik 6) ve a - Benzoilamino - 3 - ( 3 , 4-dimetoksifenil)sinnamik asit (Bileşik 7) bileşikleri uygun azlaktonlarının hidrolizi üzerinden hazırlanmıştır. Ayrıca, sentezlenen altı bileşiğin Pd/ C ile hidrojenasyonundan; 3-(3,4-Dimetoksifenil)propanoik asit (Bileşik 8); Metil 3-(3,4-Dimetoksifenil)propanoat (Bileşik 9); 2-Asetilamino-3-(3,4-dimetoksilfenil)propanoik asit (Bileşik 10) ; 2-Asetilamino-3-(3,4-di-O-asetilfenil)propanoik asit (Bileşik 11) ve 2-Benzoilamino-3-(3,4-dimetoksifenil)propanoik asit (Bileşik 12) bileşikleri olmak üzere beş indirgenme ürünü tespit edilmiştir.
THE SYNTESIS OF a-HALO-3,4-DISUBSTITUECINNAMATE AND a-ACYLAMINO-3,4-DISUBSTITUECINNAMIC ACID COMPOUNDS AND THEIR REDUCTION PRODUCT BY USING Pd/ C In this study six substrates, three of which are original, were prepared with classical organic synthesis methods. These substrates are derivatives of cinnamic acid and are procompounds of levo dopa. Three of these prochiral substrates, which are Ethyl a-bromo-3,4-dimetoxycinnamate (Compound 2); Ethyl a-chloro- 3,4-dimetoxycinnamate (Compound 3); Ethyl a-bromo-3,4-dihydroxycinnamte (Compound 4) were synthesized for the first time in this study by using Wittig Reaction. The three other substrates, which are a-Acetylamino-3-(3,4-dimetoxyphenyl)cinnamic acid (Compound 5); a-Acetylamino-3-(3,4-di-O-acetylphenyl)cinnamic acid (Compound 6); a-Benzoylamino-3-(3,4-dimetoxyphenyl)cinnamic acid (Compound 7) were prepared via hydrolysis of suitable azlactons. By using Pd/ C, synthesized six compounds were reduced and the following five reduced compounds were obtained; 3-(3,4-dimetoxyphenyl)propanoic acid (Compound 8); Methyl 3 - 3 , 4 - (dimetoxyphenyl)propanoat (Compound 9); 2 - Acetylamino - 3 - ( 3 , 4-dimetoxyphenyl)propanoic acid ( Compound 10 ) ; 2-Acetylamino - 3 - (3 , 4 -di-O-acetylphenyl)propanoic acid (Compound 11) ; 2 - Benzoylamino - 3 - ( 3 , 4 - dimetoxyphenyl)propanoic acid (Compound 12) .
THE SYNTESIS OF a-HALO-3,4-DISUBSTITUECINNAMATE AND a-ACYLAMINO-3,4-DISUBSTITUECINNAMIC ACID COMPOUNDS AND THEIR REDUCTION PRODUCT BY USING Pd/ C In this study six substrates, three of which are original, were prepared with classical organic synthesis methods. These substrates are derivatives of cinnamic acid and are procompounds of levo dopa. Three of these prochiral substrates, which are Ethyl a-bromo-3,4-dimetoxycinnamate (Compound 2); Ethyl a-chloro- 3,4-dimetoxycinnamate (Compound 3); Ethyl a-bromo-3,4-dihydroxycinnamte (Compound 4) were synthesized for the first time in this study by using Wittig Reaction. The three other substrates, which are a-Acetylamino-3-(3,4-dimetoxyphenyl)cinnamic acid (Compound 5); a-Acetylamino-3-(3,4-di-O-acetylphenyl)cinnamic acid (Compound 6); a-Benzoylamino-3-(3,4-dimetoxyphenyl)cinnamic acid (Compound 7) were prepared via hydrolysis of suitable azlactons. By using Pd/ C, synthesized six compounds were reduced and the following five reduced compounds were obtained; 3-(3,4-dimetoxyphenyl)propanoic acid (Compound 8); Methyl 3 - 3 , 4 - (dimetoxyphenyl)propanoat (Compound 9); 2 - Acetylamino - 3 - ( 3 , 4-dimetoxyphenyl)propanoic acid ( Compound 10 ) ; 2-Acetylamino - 3 - (3 , 4 -di-O-acetylphenyl)propanoic acid (Compound 11) ; 2 - Benzoylamino - 3 - ( 3 , 4 - dimetoxyphenyl)propanoic acid (Compound 12) .