Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
نویسندگان
چکیده
We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34–81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. transformation probably proceeds through cyclization iminyl formed by addition on cyclopropene double bond, followed ring-opening fragmentation.
منابع مشابه
Synthesis of 1,2-Diketones via a Metal-Free, Visible-Light-Induced Aerobic Photooxidation of Alkynes.
1,2-Diketones were synthesized by the oxidation of corresponding alkynes using air as the oxidant under metal-free conditions upon irradiation of blue light. A cheap and readily available organic dye, eosin Y, was used as the photocatalyst. For various substituents on the aryl ring, the reaction proceeded smoothly to give the dicarbonylation products in moderate to good yields. Some oxidation-s...
متن کاملromantic education:reading william wordsworths the prelude in the light of the history of ideas
عصر روشنگری زمان شکل گیری ایده های مدرن تربیتی- آموزشی بود اما تاکید بیش از اندازه ی دوشاخه مهم فلسفی زمان یعنی عقل گرایی و حس گرایی بر دقت و وضوح، انسان عصر روشنگری را نسبت به دیگر تواناییهایش نابینا کرده و موجب به وجود آمدن افرادی تک بعدی شد که افتخارعقلانیتشان، تاکید شان بر تجربه فردی، به مبارزه طلبیدن منطق نیاکانشان وافسون زدایی شان از دنیا وتمام آنچه با حواس پنجگانه قابل درک نبوده و یا در ...
Metal-free aerobic one-pot synthesis of substituted/annulated quinolines from alcohols via indirect Friedländer annulation.
Metal-free, operationally simple, and highly efficient one-pot aerobic process for the synthesis of functionalized/annulated quinolines is devised from easily available 2-aminobenzyl alcohol/2-aminobenzophenones and alkyl/aryl alcohols for the first time. The process involves two sequential reactions, namely in situ aerial oxidation of alcohols to the corresponding aldehydes/ketones followed by...
متن کاملA visible-light-mediated synthesis of carbazoles.
Carbazole, discovered over 100 years ago, is a privileged heterocyclic motif whose electronic and structural features have allowed its derivatives to find numerous applications. In addition to its abundance in natural products and bioactive molecules, carbazole has been a key motif in the development of organic light-emitting materials because of its wide band gap, high luminescent efficiency, ...
متن کاملVisible-light-mediated radical oxydifluoromethylation of olefinic amides for the synthesis of CF2H-containing heterocycles.
The visible-light-mediated oxydifluoromethylation of olefinic amides with difluoromethyl sulfones has been explored. This method allows for an efficient and practical synthesis of a variety of CF2H-containing benzoxazines and oxazolines bearing various functional groups under mild conditions.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Organic Letters
سال: 2021
ISSN: ['1523-7060', '1523-7052']
DOI: https://doi.org/10.1021/acs.orglett.1c01775