شیمى کاربردى روز

شیمى کاربردى روز

روش جدید برای سنتز 5-آمینو-[3',4-بای‌پیریدین]-6-(1H)-اون (آمرینون) با استفاده از استامیدهای α-استخلاف شده

نوع مقاله : مقاله علمی پژوهشی

نویسندگان
1 گروه شیمی، دانشگاه پیام نور، تهران، ایران
2 گروه شیمی، دانشکده علوم، دانشگاه فردوسی مشهد، مشهد، ایران
چکیده
هدف این پژوهش بررسی روش‌های جدید سنتز آمرینون بوده که در دو مسیر سنتزی متفاوت مورد بررسی قرار می‌گیرد. مسیر اول مطابق با متون قدیمی شیمی بوده که در مرحله‌ی اول پیریدین-4-استیک‌اسید با معرف ویلز-مایر واکنش داده (بهره = 2/87%) و محصول تولید شده در مرحله‌ی بعد، با سیانواستامید در شرایط قلیایی وارد واکنش شده (بهره = 3/90%)، سپس در مرحله‌ی سوم گروه نیتریل در شرایط اسیدی هیدرولیز شده (5/92%) و مرحله‌ی چهارم شامل حذف هافمن است (9/59%). ساختار آمرینون سنتز شده با استفاده از طیف‌سنجی FT-IR و 1HNMR تأیید شد. در مسیر دوم ابتدا 2-نیترو استامید طی یک واکنش تک‌ظرفی سنتز شده (4/90%) و سپس با 3-(دی‌متیل‌آمینو)-2-(پیریدین-4-ایل)آکریل‌آلدهید (2) درشرایط قلیایی واکنش داده و 5 -نیترو-[3, '4-بای‌پیریدین]-6-(1H)-اون (9) سنتز می‌شود (4/89%). در این روش جدید از اتانول به عنوان حلال و از پتاسیم‌هیدروکسید به عنوان باز استفاده شده که هر دو ترکیب ارزان و در دسترس هستند. گروه نیترو در ساختار پیش‌ماده‌ سنتز شده با استفاده از گاز هیدروژن در حضور کاتالیزگر فلزی قابل کاهش بوده و می‌توان آمرینون با بازده و خلوص بالا سنتز کرد. نتایج نشان داد که روش جدید ارائه شده، مزایای متعددی داشته که می‌توان به مواردی همچون کاهش تعداد مراحل واکنش، خالص‌سازی آسان‌تر، استفاده از مواد اولیه و حلال‌های ارزان قیمت و در دسترس، افزایش سرعت و نیز افزایش بازده اشاره نمود. در مجموع، این پژوهش نشان داد که روش سنتزی جدید می‌تواند به عنوان یک روش جایگزین مناسب برای روش‌های قبلی مورد استفاده قرار گیرد و به تولید کارآمدتر آمرینون کمک شایانی کند.
کلیدواژه‌ها
موضوعات

عنوان مقاله English

A new method for the synthesis of 5-Amino-[3,4'-bipyridin]-6-(1H)-one (Amrinone) by use of α-Substituted Acetamides

نویسندگان English

Ziant Gordi 1
Abolfazl Shakhs-salim 1
Iman Farzamnezhad 2
1 Department of chemistry, Payam noor university, Tehran, Iran
2 Department of chemistry, Faculty of science, Ferdowsi University of Mashhad, Mashhad, Iran
چکیده English

This research aims to develop novel synthetic methods for amrinone through two distinct synthetic pathways. The first pathway, based on established chemical protocols, involves a four-step reaction sequence. Initially, pyridine-4-acetic acid reacts with the Vilsmeier reagent, followed by condensation with cyanoacetamide under alkaline conditions. The nitrile group is then hydrolyzed under acidic conditions, and the final step involves a Hofmann rearrangement. The structure of the synthesized amrinone was confirmed using FT-IR and 1HNMR spectroscopy. The second pathway begins with the one-pot synthesis of 2-nitroacetamide, which is subsequently reacted with 3-(dimethylamino)-2-(pyridin-4-yl)acrolein under alkaline conditions to produce 5-nitro-[3’,4’-bipyridin]-6-(1H)-one, an amrinone precursor. This method employs ethanol as a solvent and cost-effective potassium hydroxide as the base. The nitro group in the precursor is reduced using hydrogen gas in the presence of a metal catalyst, yielding amrinone with high purity and efficiency. The proposed methods offer several advantages, including fewer reaction steps, simplified purification, use of inexpensive and readily available starting materials and solvents, enhanced reaction speed, and improved yields. Overall, this study demonstrates that the newly developed synthetic approaches provide a more efficient and practical alternative to existing methods, significantly enhancing the production of amrinone.

کلیدواژه‌ها English

Amrinone
Acetamide
New Synthesis
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