Synthesis of Phenolic Compounds by Trapping Arynes with a Hydroxy Surrogate.
نویسندگان
چکیده
Trapping of arynes with various nucleophiles provides a range of heteroatom-functionalized arene derivatives, but the corresponding reaction with water does not provide phenol derivatives. Silver trifluroacetate (AgO₂CCF₃) can nicely solve this problem. It was found that in typical organic solvent, AgO₂CCF₃ readily reacts with arynes to generate trifluoroacetoxy organosilver arene intermediate, which, upon treating with silica gel, provides phenolic products. This protocol can be extended to the synthesis of α-halofunctionalized phenol derivatives by simply adding NBS (N-bromosuccinimides) or NIS (N-iodosuccinimides) to the reaction along with silver trifluroacetate, which provided α-bromo or α-iodophenol derivatives in good yield. However, the similar reactions with NCS (N-chlorosuccinimides) afforded only the protonated product instead of the expected α-chlorophenols derivatives. Interestingly, substrates containing silyl substituents on 1,3-diynes resulted in α-halotrifluoroacetates rather than their hydrolyzed product. Additionally, trapping the same arynes with other oxygen-based nucleophiles containing silver counter cation, along with NXS (N-halosuccinimides), generated α-halooxyfunctionalized products.
منابع مشابه
A CONVENIENT AND GENERAL SYNTHESIS OF THIADIAZOLO [2,3-C] [1,2,4] TRIAZINES
Condensation and cyclization of 5-hydroxy- 1,2,4- thiadiazol-2-yl hydrazine 1 with pyruvic acid, phenacyl bromide, propargyl bromide and ally1 bromide afforded compounds 2,5,7 3, 4 ,6 and 8 respectively, Reaction of 1 with epichforohydrine afforded 4-hydroxy-N-[5-hydroxy- 1 ,3,4-thiadiazoly1] pyrazolidine 9
متن کاملSynthesis, Characterization and Antioxidant Activity of Two Novel Oxovanadium (IV) Curcuminoids
The reaction of bis[4-hydroxy-3-methoxyphenyl]-1,6-heptadiene-3,5-dione (curcumin) and two novel ligands of bis[4-tetrabenzylglucose-3-methoxyphenyl]-1,6-heptadiene-3,5-dione (bis(tetrabenzylglucose)curcumin) (BTBGC) and bis[4-tetraacetylglucose-3-methoxyphenyl]-1,6-heptadiene-3,5-dione (bis(tetraacetylglucose)curcumin) (BTAGC) with vanadium in methanol, in a 2:1 molar ratio, which yield the co...
متن کاملThe Evaluation of Antioxidant Activities and Phenolic Compounds in Leaves and Inflorescence of Artemisia dracunculus L. by HPLC
Background: Artemisia dracunculus L. belongs to the Anthemideae tribe of Asteraceae family. This plant has been used in traditional folk medicine. Also, it's anti-bacterial, anti-fungal, antioxidant, anti-inflammatory and hepatoprotective activity has been proved. Objective: The purpose of this study was to evaluate the antioxidant activity of leaves and inflorescence of A. dracunculus and als...
متن کاملSynthesis of a novel radical trapping and carbonyl group trapping anti-AGE agent: a pyridoxamine analogue for inhibiting advanced glycation (AGE) and lipoxidation (ALE) end products.
[structure: see text] Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained durin...
متن کاملمقایسه محتوای ترکیبات فنلی، فلاونوئیدی و فعالیت آنتیاکسیدانی اندام هوایی دو جمعیت گیاه بشقابی سنبلهای (Scutellaria Pinnatifida) در شمال ایران
Background and Objective: Phenolic acids, polyphenols and flavonoids are antioxidant compounds, which act as cell protective factors against oxidative stress by trapping and inhibition of free radicals, play an important role in plants and animals health. In this research, in order to optimize extraction of antioxidant compounds, phenolic and flavonoid contents and antioxidant activity of...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Molecules
دوره 20 9 شماره
صفحات -
تاریخ انتشار 2015