سنتز کارآمد و جدید مولکول های هیبریدی ایندن-پیرول ها در آب
محورهای موضوعی : شیمی آلیعطیه رضوانیان 1 * , زهرا آلبوغبیش 2
1 - استادیار گروه شیمی آلی، دانشکده شیمی، دانشگاه الزهرا، تهران، ایران.
2 - دانشجوی کارشناسی ارشد گروه شیمی آلی، دانشکده شیمی، دانشگاه الزهرا، تهران، ایران.
کلید واژه: : شیمی سبز, مولکول¬های هیبریدی آلی, ایندن-پیرول¬ها, نین‌هیدرین, استوفنون, انامین.,
چکیده مقاله :
در این پژوهش، روش جدیدی برای سنتز مولکولهای هیبریدی ایندن-پیرول‌ها با بهرهگیری از مزیت‌های واکنش‌های چندجزئی مانند سادگی روش انجام واکنش، استفاده از حلال کمتر، زمان کوتاه و نیز بی‌نیازی به جداسازی هرگونه حدواسط با بازده بالا ارائه میشود. واکنش چهارجزئی تک ظرف بین نین‌هیدرین، استوفنون، آمین نوع اول و اتیل استواستات در حلال آب و در دمای 60 درجه سلسیوس در حضور سدیم هیدروکسید منجر به سنتز مولکولهای هیبریدی ایندن-پیرول میشود. به این صورت که ابتدا از واکنش نین‌هیدرین با استوفنون در محیط بازی حدواسط الکترون‌دوست ایجاد میشود. سپس، با انجام واکنش تراکمی میان آمین نوع اول و اتیل استواستات حدواسط انامینونی تشکیل میشود. در ادامه با حمله هسته‌دوستی و افزایش مایکل حدواسط انامینونی به حدواسط الکترون‌دوست و پس از آن حمله هسته‌دوستی درون مولکولی گروه امینی به کربونیل کتون، موجب تشکیل حلقه پنج ضلعی میشود. در پایان با حذف آب، مشتق هیبریدی ایندن-پیرول بهدست آمد.
In this research, a new method for the synthesis of hybrid indene-pyrroles molecules is presented with high efficiency by taking advantages of the multicomponent reactions, such as the simplicity of the reaction method, the use of less solvent, and shorter reaction time. In this method, there is no need to separate any intermediates. The one-pot four-component reaction between ninhydrin, acetophenone, first-type amine and ethyl acetoacetate in water solvent at 60 °C in the presence of sodium hydroxide led to the synthesis of indene-pyrrole hybrid molecules. In this way, an electrophilic intermediate was created from the reaction of ninhydrin with acetophenone in the playing medium. Then, an enamine intermediate was formed by performing a condensation reaction between the first type amine and ethyl acetoacetate. Next, with the nucleophilic attack and Michael increase of the enamino intermediate to the electrophilic intermediate and then the intramolecular nucleophilic attack of the amine group on the carbonyl ketone, a pyrrole ring was formed. Finally, the indene-pyrrole hybrid derivative was obtained by removing water
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