Synthesis of new derivatives of 2-alkynylamino-6-substituted-pyrimidine- 5-carbaldehyde catalyzed by Pd-Cu

سال انتشار: 1397
نوع سند: مقاله کنفرانسی
زبان: انگلیسی
مشاهده: 297

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شناسه ملی سند علمی:

IRANCC20_658

تاریخ نمایه سازی: 28 اردیبهشت 1398

چکیده مقاله:

Pyrimidine derivatives are one of the most broadly distributed groups of natural compounds. Most pyrimidine-trione derivatives have several biological properties such as the anti-tumor, anti-cancer, HIV-1 and HIV-2 protease inhibitors, anticonvulsant, and anti-osteoporosis activities [1]. In the last few decades, the concept of catalyzed cascade reactions has been commenced through the advent of transition metal catalysis. Although many transition metal complexes have been found to efficiently catalyze cascade and sequential reactions, palladium complexes are clearly privileged and of paramount importance [3]. The Sonogashira coupling reaction catalyzed by palladium and copper is a powerful and straightforward method for the construction of arylated internal alkynes [4]. In this study, the reaction of 4- chloro-6-substituted-pyrimidine-5-carbaldehyde with various propargylamines catalyzed by Pd–Cu in the presence of triethyl amine as the base in CH3CN leads to the one-pot formation of novel series of 2-alkynylamino-6-substituted-pyrimidine-5- carbaldehyde in moderate-to-high yields.A mixture of 4-chloro-6-substituted-pyrimidine-5-carbaldehyde (1 mmol), PdCl2(PPh3)2 (3.5 mol%), CuI (7 mol%), and Et3N (2 mmol) was stirred in CH3CN (5 mL) at room temperature for 20 min under an argon atmosphere. Propargylamines (1.2 mmol) was then added and the mixture was stirred at room temperature for 5 h. After completion of the reaction, the resulting solution was concentrated in vacuo, and the crude product was subjected to silica gel column chromatography using nhexane: ethyl acetate (9:1) as the eluent to afford the pure product

نویسندگان

Fatemeh Rezaeemanesh

Department of Chemistry, Faculty of Science, shahrood University of Technology, shahrood, Iran

Mohammad bakherad

Department of Chemistry, Faculty of Science, shahrood University of Technology, shahrood, Iran

Hossein Nasr-Isfahani

Department of Chemistry, Faculty of Science, shahrood University of Technology, shahrood, Iran