Synthesis of Thiazole and Thiazine Derivative Compounds Obtained From New Thioxopyrimidine Compound, Investigation of Their Reactions With Substituted Aldehydes and Examining of Their Theoretically Electronic Properties

Abstract

Çalışmamızın ilk aşamasında multikomponent reaksiyonlardan biri olan Biginelli reaksiyonuyla, 1,3-difenil-1,3-propandion, 2,4-dimetoksibenzaldehit ve tiyoüre kullanılarak (4-(2,4-dimetoksifenil)-6-fenil-2-tiyokso-1,2,3,4-tetrahidropirimidin-5-il)(fenil)metanon (D-1) bileşiği sentezlendi. D-1 bileşiğinin bromopiruvik asit, 3-bromopropiyonik asit ve bromoasetik asit ile halkalanma tepkimeleri gerçekleştirilerek, pirimidin halkasına kondense tiyazin ve tiyazol (D-2, D-3 ve D-4) bileşikleri elde edildi. Son basamakta ise 6-benzoil-5-(2,4-dimetoksifenil)-7-fenil-5H-tiyazolo[3,2-a]pirimidin-3(2H)-on (D-4) bileşiğinin, sübstitüe benzaldehit türevleri ve 2-tiyofenkarboksaldehit bileşikleriyle tepkimeleri gerçekleştirildi. Sentezlenen tüm bileşiklerin teorik hesaplamaları ve moleküler elektrostatik potansiyel haritaları Gaussian paket programı kullanılarak Density Functional Theory (DFT/6-31G) teorisi ve B3LYP fonksiyonelleri ile incelendi. Elde edilen tüm pirimidin türevi bileşiklerin yapısal karakterizasyonları, elementel analiz, IR, 1H ve 13C NMR spektroskopik yöntemler kullanılarak aydınlatıldı.

In the first stage of our study, using Biginelli reaction, which is one of the multicomponent reactions, using 1,3-diphenyl-1,3-propanedione, 2,4-dimethoxybenzaldehyde and thiourea the compound (4-(2,4-dimethoxyphenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)(phenyl) methanone (D-1) was synthesized. The cyclization reactions of D-1 compound with bromopyruvic acid, 3-bromopropionic acid and bromoacetic acid were carried out to obtain thiazine and thiazole (D-2, D-3 and D-4) compounds condensed to the pyrimidine ring. In the last step, the compound 6-benzoyl-5-(2,4-dimethoxyphenyl)-7-phenyl-5H-thiazolo [3,2-a] pyrimidin-3(2H)-one (D-4), reactions were carried out with substituted benzaldehyde derivatives and 2-thiophenecarboxaldehyde compounds. The theoretical calculations and molecular electrostatic potential maps of all synthesized compounds were examined with Density Functional Theory (DFT / 6-31G) theory and B3LYP functionalities using Gaussian software package. The structural characterizations of all pyrimidine derivatives obtained were elucidated using elemental analysis, IR, 1H and 13C NMR spectroscopic methods.