DMF as a trifunctional organocatalyst: one-pot seven-component sequential synthesis of novel derivatives of tetrazoloquinolone-containing aminofuropyrimidines
Elham Batebi - Nazanin Abidzadeh - Mohammad Bagher Teimouri
Elham Batebi - Nazanin Abidzadeh - Mohammad Bagher Teimouri
Faculty of Chemistry, Kharazmi University, Tehran, Iran - Faculty of Chemistry, Kharazmi University, Tehran, Iran - Faculty of Chemistry, Kharazmi University, Tehran, Iran
زبان مقاله : انگلیسی |
تعداد صفحات مقاله : 1 صفحه |
نوع مقاله : چکیده |
ISC کد مقاله در : ISC4026_524654
چکیده
Organocatalysis is a really attractive tool for performing effective reactions while avoiding the use of metals.[1] Normally, organocatalysts contaminate less and are less toxic than organometallic catalysts because they do not include metals within their structures, which is beneficial for industries that try to avoid using metals, such as the pharmaceutical industry. N,N-Dimethylformamide (DMF) is a versatile and multipurpose reagent which can has so many roles in chemical transformations.[2] Often used as a common solvent for chemical reactions and utilized widely in industry as a reagent, it has played an important role in organic synthesis for a long time. It is also a common organocatalyst used in the synthesis of a wide range of organic compounds. The furopyrimidine ring system is found in a broad range of biologically active compounds.[3] Specifically, the furo[2,3-d]pyrimidines are an important class of annulated uracils with biological significance because of their connection with purine systems. It has numerous pharmacological and agrochemical applications viz. Akt1 kinase inhibitors, antifolates, and antivirus, as well as potential radiation protection agents. Due to their biological importance, furo[2,3-d]pyrimidine derivatives have become synthetic targets for many organic and medicinal chemists. On the other hand, the tetrazole group has considered analogous to carboxylic group as a pharmacophore. Several substituted tetrazoles show pronounced activities including antimicrobial, antimycobacterial, antiproliferative, anticancer and multi-drug resistance, etc.[4] The fusion of quinoline to the tetrazole ring is known to increase the biological activity.[5] In particular, tetrazolo[1,5-a]quinoline-4-carbaldehyde serves as a key synthetic intermediate for the synthesis of novel medicinally valuable compounds.[5] Encouraged by their potential clinical applications and in continuation of our previous investigations on bio-potent complex heterocycles,[6] our efforts are focused to design and synthesize more biologically potent heterocyclic systems via combination of diverse therapeutically active moieties quinoline, tetrazole, furan and pyrimidindine together in a single scaffold. Herein, we report the synthesis of 2-chloroquionoline-3-carbaldehyde by a Vilsmeier–Haack formylation of acetanilide and phosphorus oxychloride in DMF and the sequential addition of sodium azide, acetic acid, barbituric acid and isocyanide to yield tetrazoloquinolone-containing aminofuropyrimidines in a one-pot seven-component Vilsmeier–Haack formylation/[3+2] cycloaddition/Knoevenagel condensation/[4+1] cycloaddition/tautomerization sequential reaction. High rates of reactions at room temperature have led us to establish a significant catalytic role for DMF in the Knoevenagel condensation stage. Eight new bonds and three new heterocycles were assembled in a facile one-pot operation.کليدواژه ها
Organocatalysis, DMF, Tetrazoloquinoline-4-carbaldehyde, Multicomponent reactions, Furopyrimidinesنحوه استناد به مقاله
در صورتی که می خواهید در اثر پژوهشی خود به این مقاله ارجاع دهید، به سادگی می توانید از عبارت زیر در بخش منابع و مراجع استفاده نمایید:Batebi , Elham , 1398 , DMF as a trifunctional organocatalyst: one-pot seven-component sequential synthesis of novel derivatives of tetrazoloquinolone-containing aminofuropyrimidines , دومین کنفرانس ملی کاتالیست انجمن شیمی ایران
انتشار دهنده
محل انتشار : دومین کنفرانس ملی کاتالیست انجمن شیمی ایرانمشخصات برگزارکننده همایش : دانشگاه خوارزمي
تعداد مقالات : 215
کد اختصاصی :
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