Synthesis of Chalcone-dimethyl 1,2,3-triazole-4,5-dicarboxlate Structures

Koldaş S., Yağız Erdemir G., Altundaş A.

The 12th International Drug Chemistry Congress, Antalya, Türkiye, 7 - 10 Mart 2024, ss.155

Yayın Türü: Bildiri / Özet Bildiri
Basıldığı Şehir: Antalya
Basıldığı Ülke: Türkiye
Sayfa Sayıları: ss.155
Gazi Üniversitesi Adresli: Evet

Özet

Chalcones, found in plants, are characterized by open-chain structures that incorporate 1,3-diaryl groups linked to a three-carbon α,β-unsaturated carbonyl structure.¹ Chalcones, with their diverse biological activities, play a crucial role in various pharmacological applications such as the development of novel drugs and therapeutic agents. Triazoles, a significant class of azole compounds, have become more accessible in the literature, largely due to the Click chemistry method pioneered by Sharples.The structural resem blance of this skeletal configuration to peptide bonds has facilitated extensive exploration, particularly in the field of medicinal chemistry.Upon examining the literature featuring these crucial skeletal structures, it was reported that Triazole chalcone hybrid molecules exhibited effective in vivo studies.² In line with this literature insight, firstly 1,4,5-trisubstituted-1,2,3-triazoles were synthesized, and then triazole-chalcone hybrid molecules containing the chalcone skeleton on structure from the 1-position of the 1,2,3-triazole. Notably, the targeted 1,2,3-triazole- chalcone hybrid molecules were synthesized with high yields, obviating the need for a metal catalyst and avoid in purification techniques like column chromatography. In this study, we synthesized 14 new chalcone-1,2,3-triazole hybrid molecules that we think may exhibit biological effective properties. For this aim first of all, 4-acetylphenzylazide compound was synthesized from 4-acetylaniline and then 4-acetylphenzylazide reacted with benzaldehyde 1a-k using the Claisen-Schmidt method gave 1-(4-azidophenyl)-3-phenlyprop-2-en-1-ones. After that [3+2] cycloaddition of this compound with dimethyl acetylenedicarboxylate gave target molecules dimethyl 1-(4-cinnamoylphenyl)-1H-1,2,3-triazole-4,5-dicarboylate between 24-79% yields. The structures of all new synthesized compounds were characterized using IR, ¹ H and ¹³ CNMR spectroscopic methods.